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Advances in Organometallic Chemistry Vol 48 1st Edition
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 Advances in
ORGANOMETALLIC CHEMISTRY

VOLUME 48
This Page Intentionally Left Blank
 Advances in
Organometallic
Chemistry
EDITED BY

ROBERT WEST ANTHONY F. HILL

DEPARTMENT OF CHEMISTRY DEPARTMENT OF CHEMISTRY
UNIVERSITY OF WISCONSIN IMPERIAL COLLEGE OF SCIENCE
MADISON, WISCONSIN TECHNOLOGY, AND MEDICINE
LONDON, ENGLAND

FOUNDING EDITOR

F. GORDON A. STONE

VOLUME 48

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01 02 03 04 05 06 EB 9 8 7 6 5 4 3 2 1
 Contents

CONTRIBUTORS . . . . . . . . . . . . . . . . . . . . . . . . . . . vii

Metal Complexes of Stable Carbenes

WOLFGANG HERMANN, THOMAS WESKAMP,
and VOLKER P. W. BÖHM

I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 1
II. Metal Complexes . . . . . . . . . . . . . . . . . . . . . . . . 8
III. Applications in Homogeneous Catalysis . . . . . . . . . . . . . . . 35
IV. Other Applications . . . . . . . . . . . . . . . . . . . . . . . . 55
V. Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
References . . . . . . . . . . . . . . . . . . . . . . . . . . . 59

Transition Metal Chemistry of 1,3-Diynes, Poly-ynes,

and Related Compounds

PAUL J. LOW and MICHAEL I. BRUCE

I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 72
II. Diynyl Complexes, M{(C C)2 R}n (n = 1, 2) . . . . . . . . . . . . . 74
III. Di- and Poly-yne π Complexes with One or Two Metal Centers . . . . . . 102
IV. Metal Cluster Complexes Derived from 1,3-Diynes or Poly-ynes . . . . . . 130
V. σ ,π-Diynyl Complexes . . . . . . . . . . . . . . . . . . . . . . 164
VI. σ ,π-Diyne Complexes of Groups 3, 4, and 5 . . . . . . . . . . . . . . 177
VII. Other Reactions of Diynes with Metal Complexes . . . . . . . . . . . . 199
VIII. Formation of Free Di- and Poly-ynes by Reactions at Metal Centers . . . . . 224
IX. Ligands Containing Diyne Groups . . . . . . . . . . . . . . . . . . 226
X. Spectroscopic Properties, Electronic Structure, and Redox Behavior . . . . . 241
XI. Metalladiynes and Related Complexes . . . . . . . . . . . . . . . . 254
XII. Polymer and Materials Chemistry . . . . . . . . . . . . . . . . . . 262
XIII. Prognosis . . . . . . . . . . . . . . . . . . . . . . . . . . . 263
XIV. Appendix: Abbreviations . . . . . . . . . . . . . . . . . . . . . 265
XV. Addendum . . . . . . . . . . . . . . . . . . . . . . . . . . . 266
References . . . . . . . . . . . . . . . . . . . . . . . . . . . 270

v
vi Contents

Organoelement Chemistry of Main Group

Porphyrin Complexes
PENELOPE J. BROTHERS

I. Introduction . . . . . . . . . . . . . . . . . . . .
. . . . . . 289
II. Boron . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . 294
III. Aluminum . . . . . . . . . . . . . . . . . . . . .
. . . . . . 295
IV. Gallium, Indium, and Thallium . . . . . . . . . . . . .
. . . . . . 303
V. Silicon, Germanium, and Tin . . . . . . . . . . . . . .
. . . . . . 311
VI. Phosphorus, Arsenic, and Antimony . . . . . . . . . . .
. . . . . . 321
VII. Main Group Porphyrin Complexes Containing Metal Metal Bonds . . . . . 331
References . . . . . . . . . . . . . . . . . . . . . . . . . . . 337

INDEX . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 343
CUMULATIVE LIST OF CONTRIBUTORS FOR VOLUMES 1–36 . . . . . . . . . . 349
CUMULATIVE INDEX FOR VOLUMES 37–48 . . . . . . . . . . . . . . . . . 353
 Contributors

Numbers in parentheses indicate the pages on which the authors’ contributions begin.

VOLKER P. W. BÖHM (1), Department of Chemistry, University of North Carolina at

Chapel Hill, Chapel Hill, North Carolina 27599
PENELOPE J. BROTHERS (289), Department of Chemistry, The University of Auckland,
Auckland, New Zealand
MICHAEL I. BRUCE (71), Department of Chemistry, University of Adelaide, Adelaide,
South Australia 5005, Australia
WOLFGANG A. HERRMANN (1), Anorganisch-chemisches Institut der Technischen
Universität München, D-85747 Garching bei München, Germany
PAUL J. LOW (71), Department of Chemistry, University of Durham, Durham DH1 3LE,
England
THOMAS WESKAMP (1), Symyx Technologies, Santa Clara, California 95051

vii
This Page Intentionally Left Blank
 ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL. 48

Metal Complexes of Stable Carbenes*

WOLFGANG A. HERRMANN
Anorganisch-chemisches Institut der Technischen Universität München
D-85747 Garching bei München, Germany

THOMAS WESKAMP
Symyx Technologies
Santa Clara, California 95051

VOLKER P. W. BÖHM
Department of Chemistry
University of North Carolina at Chapel Hill
Chapel Hill, North Carolina 27599-3290
I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
A. Historic Background . . . . . . . . . . . . . . . . . . . . . . . 1
B. Stable Carbenes . . . . . . . . . . . . . . . . . . . . . . . . . 3
C. Precursors for Stable Carbenes . . . . . . . . . . . . . . . . . . . 5
II. Metal Complexes . . . . . . . . . . . . . . . . . . . . . . . . . . 8
A. Main-Group Metal Complexes . . . . . . . . . . . . . . . . . . . 8
B. Transition Metal Complexes . . . . . . . . . . . . . . . . . . . . 11
C. Properties of NHC Ligands . . . . . . . . . . . . . . . . . . . . . 31
III. Applications in Homogeneous Catalysis . . . . . . . . . . . . . . . . . 35
A. Olefin Metathesis . . . . . . . . . . . . . . . . . . . . . . . . 36
B. Heck-Type Reactions . . . . . . . . . . . . . . . . . . . . . . . 42
C. Other Reactions . . . . . . . . . . . . . . . . . . . . . . . . . 47
D. Heterogenization . . . . . . . . . . . . . . . . . . . . . . . . . 51
E. Asymmetric Catalysis . . . . . . . . . . . . . . . . . . . . . . . 53
F. High-Throughput Screening . . . . . . . . . . . . . . . . . . . . 54
IV. Other Applications . . . . . . . . . . . . . . . . . . . . . . . . . . 55
A. Materials Science . . . . . . . . . . . . . . . . . . . . . . . . 55
B. Bioinorganic Chemistry . . . . . . . . . . . . . . . . . . . . . . 56
C. Medicinal Chemistry . . . . . . . . . . . . . . . . . . . . . . . 57
V. Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59

I
INTRODUCTION

A. Historic Background

Carbenes—molecules with a neutral dicoordinate carbon atom—have played an

important role in organic chemistry ever since their first firm evidence of existence.

∗ Dedicated to Professor Henri Brunner on the occasion of his 65th birthday.

1
Copyright C 2001 by Academic Press, Inc.

All rights of reproduction in any form reserved.

0065-3055/01 $35.00
2 HERRMANN et al.

However, despite the increasing interest in persistent intermediates since the days
of Gomberg1,2 and despite the fact that carbenes were introduced into organic
chemistry by Doering and Hoffmann in the 1950s3 and into organometallic chem-
istry by Fischer and Maasböl in the 1960s,4 it was only in the late 1980s and early
1990s that the first carbenes were isolated [Eq. (1)].5–8

Me3Si N N
∆ or hν Me3Si
C P C P
N2 N - N2
N

(1)
NaH
THF / cat. DMSO
-
R N N R Cl R N N R
- H2, - NaCl

R = 1-adamantyl

This discovery resulted in a revival of carbene chemistry, surprisingly more in

organometallic chemistry than in organic chemistry.9,10 One explanation for the
interest of organometallic chemists in stable free carbenes might be the fact that
the metal complexes 1 and 2 containing the subsequently isolated N-heterocyclic
carbenes were prepared as early as in 1968 by Wanzlick and Schönherr and by
Öfele.11,12

2+
CH3
Ph N N Ph
N
Hg 2 ClO4- Cr(CO)5
N
Ph N N Ph CH3

1 2

That was only 4 years after the preparation of the first Fischer-type carbene com-
plex 3,4 6 years before the first Schrock-type carbene complex 4 was reported,13
and more than 20 years before the isolation of stable imidazolin-2-ylidenes by
Arduengo in 1991 [Eq. (1)].7 Once attached to a metal, these Wanzlick- or
Arduengo-carbenes have shown a reaction pattern completely different from that
 Metal Complexes of Stable Carbenes 3

of the electrophilic Fischer- and nucleophilic Schrock-type carbene complexes.

CH3
O H3C
C W(CO)5 Ta
R H2 C

3 4

This article presents the principles known so far for the synthesis of metal
complexes containing stable carbenes, including the preparation of the relevant
carbene precursors. The use of some of these compounds in transition-metal-
catalyzed reactions is discussed mainly for ruthenium-catalyzed olefin metathesis
and palladium-/nickel-catalyzed coupling reactions of aryl halides, but other reac-
tions will be touched upon as well. Chapters about the properties of metal– carbene
complexes, their applications in materials science and medicinal chemistry, and
their role in bioinorganic chemistry round the survey off. The focus of this review
is on N-heterocyclic carbenes, in the following abbreviated as NHC and NHCs,
respectively.

B. Stable Carbenes

Wanzlick et al. realized in the 1960s that the stability of carbenes should be
increased by a special substitution pattern of the disubstituted carbon atom.14–16
Substituents in the vicinal position that provide π -donor/σ -acceptor character to
“fill” the p-orbital of the carbene carbon and stabilize the carbene lone pair by a
negative inductive effect should reduce the electrophilicity of the singlet carbene
and consequently reduce its reactivity (Scheme 1).
Based on this concept and the development of appropriate synthetic methods,
many heteroatom-substituted carbenes have been isolated since the first successful
attempts by Igau et al.5 and by Arduengo et al.7 The stability of carbenes was

X
R R
C C
C
R R
X

SCHEME 1. σ -Acceptors and π-donors vicinal to the carbene–carbon atom stabilize carbenes.
4 HERRMANN et al.

originally considered to be limited to cyclic diaminocarbenes (nitrogen provides

good π -donor/σ -acceptor character) with steric bulk to prevent dimerization17
and some aromatic character.18 This holds true for imidazolin-2-ylidenes as well
as for 1,2,4-triazolin-5-ylidenes. For this family of stable carbenes, many examples
have been isolated so far, among them 5–13.9,19–21 12 was even reported to be air
stable.22 Steric hindrance at the nitrogen substituents does not solely determine
whether a carbene can be isolated: the 1,3-dimethylimidazolin-2-ylidene 5 can be
distilled for its purification without significant decomposition.23 However, steric
parameters certainly influence the long-term stability of NHCs.24,25

H 3C Ph
N CH N N Ph N N CH3
H3 C N 3

5 6 7

N N N N N
N

Ph2P EtHN EtO OEt

8 9 10

Cl Cl Ph
N
N N N N N Ph
Ph N
N
11 12 13
N

Later, imidazolidin-2-ylidenes such as 14, a “saturated,” more electron-rich and

nonaromatic version of the imidazolin-2-ylidenes, were isolated.25,26 Isolation of a
six-membered tetrahydropyrimid-2-ylidene 1527,28 and of acyclic structures such
as 1629,30 was a consequent extension since these compounds still possess two
nitrogens vicinal to the carbene carbon, but lack the 6π -electron conjugation.

N N N N N N

14 15 16

For all these compounds, the carbene carbon has two nitrogen substituents,
which is in complete agreement with the consideration that strong π -donor sub-
stituents are an essential requirement for stable carbenes. However, one weaker
 Metal Complexes of Stable Carbenes 5

π-donor substituent, e.g., an alkoxy or alkylsulfido group, can be tolerated as was

demonstrated for 17–19.31

N S N S N O

17 18 19

C. Precursors for Stable Carbenes

1. Precursors for NHCs with Unsaturated Backbone (Imidazolin-2-ylidenes

and Benzimidazolin-2-ylidenes)

In many cases the synthesis of NHC complexes starts from N,N′ -disubstituted
azolium salts. Imidazolium salts as precursors for imidazolin-2-ylidenes are gen-
erally accessible by two ways complementing each other: (i) nucleophilic substi-
tution at the imidazole heterocycle or (ii) a multicomponent reaction building up
the heterocycle with the appropriate substituents in a one-pot reaction.
Imidazolium salts that can be prepared by the first procedure, the alkylation of
imidazole, are easy to obtain and often used for metal complex synthesis. Potassium
imidazolide is reacted with the first equivalent of alkyl halide in toluene to give the
1-alkylimidazole.32 Subsequent alkylation in 3-position is achieved by addition
of another equivalent of alkyl halide [Eq. (2)].33–35 A variant of this approach
employs commercially available N-trimethylsilyl imidazole with 2 equiv of an alkyl
chloride, under elimination of volatile Me3SiCl.36 The drawback of these simple
routes is the fact that only primary alkyl halides can be reacted in satisfactory
yields because secondary and tertiary alkyl halides give substantial amounts of
elimination by-products.
R-X
K+ N N N N R
- KX R N N

X-
(2)
2 R-Cl
N R
Me3Si
N N R N
- Me3SiCl
Cl-

In order to introduce other substituents at the 1- and 3-positions of the imi-

dazolium salt the reaction of primary amines with glyoxal and formaldehyde in
the presence of acid can be used [Eq. (3)].20,37,38 Variation of the amine allows
the preparation of imidazolium salt libraries which can be diversified by using
6 HERRMANN et al.

different acids in order to change the anion of the imidazolium salt.39 The use of
chiral amines in this reaction results in the convenient generation of C2-symmetric
imidazolium salts.21 It is possible to generate imidazolium salts with anilines that
do not bear a para-substituent in a two-step sequence: synthesis of the bisimine in
the first step and subsequent ring closure with formaldehyde and an acid.40,41
H H
C C
O O HX
RNH2 + H2NR R N N R X- (3)
O - 3 H2O
C
H H

A method by Gridnev and Mihaltseva allows the combination of both strate-

gies: (i) synthesis of the 1-alkylimidazole by a multicomponent reaction start-
ing from glyoxal, formaldehyde, a primary amine and ammonium chloride, and
(ii) subsequent alkylation by a primary alkyl halide to give the imidazolium salt
[Eq. (4)].42
H H
C C
O O H3PO4
RNH2 + [NH4]Cl R N N R N N (4)
O
X-
C
H H

Direct coupling of imidazole with aryl iodides in the presence of copper(I)

triflate results in 1-aryl-imidazoles, which can be alkylated in a second step
[Eq. (5)]. This route represents a variation of the Gridnev method.43

I
[Cu(OTf)]2 N N
+ HN N (5)
- 2 HI R
R

The abstraction of a hydride is an additional route for the preparation of ben-

zimidazolium salts: Treatment of 2,3-dihydro-1 H-benzimidazoles with tritylium
tetrafluoroborate generates the benzimidazolium salt and triphenylmethane
[Eq. (6)].44
R R
N H + [Ph3C][BF]4 N
H (6)
H - Ph3CH
N N [BF]4
R R

The reaction of N-alkyl-N-formyl hydrazines with imidoyl chlorides gives 3,4-

substituted 1-alkyl-4H-1,2,4-triazolium salts in a one-pot reaction.45
 Metal Complexes of Stable Carbenes 7

X NH2

+ 2 2 +
NH2 NH2 O O
R R

Pd-cat. - HX 1) - 2 H2O
2) Na[BH3(CN)]

HC(OEt)3
NH HN N N
NH4BF4
R R R R
SCHEME 2. Synthesis of imidazolidinium salts.

2. Precursors for NHCs with Saturated Backbone (Imidazolidin-2-ylidenes)

The reaction of an ortho-ester, e.g., HC(OEt)3, with a secondary bisamine in
the presence of an ammonium salt yields imidazolidinium salts (Scheme 2).46,47
The necessary secondary diamines can be generated by a classical condensation–
reduction sequence or by applying the palladium-catalyzed Buchwald–Hartwig
amination.48 The latter reaction offers convenient access to imidazolidinium salts
with chiral backbones starting from chiral diamines, a number of which are com-
mercially available.46

3. Precursors for Acyclic Carbenes

Procedures for the synthesis of precursors for acyclic diamino-, aminoxy-, and
aminothiocarbenes rely on the condensation of formamides with phenols, thiophe-
nols, and amines, respectively (Scheme 3).29–31

SH
R

R N S

R O
2
N N R C
POCl3 H NR2
R

R N O
OH

SCHEME 3. Preparation of precursors for acyclic carbenes.

8 HERRMANN et al.

Fe2(CO)9 NMe2 Fe2(CO)9

+ (OC)4Fe +
NMe2 NMe2
NMe2 S
_
Cl + Cl NMe2
NMe2
SCHEME 4. Synthetic routes to an iron complex containing an acyclic diaminocarbene.

Metal complexes of these carbenes have not been published yet, although
complexes with :C(NMe2)2 are accessible, e.g., via the routes depicted in
Scheme 4.49–55

II
METAL COMPLEXES

Metal complexes of stable carbenes are now known for almost all the metals
of the periodic table. This chapter is divided into an overview of the NHC–main-
group metal adducts that are generally synthesized by adding the free NHC to an
appropriate metal precursor and a discussion of the various synthetic approaches
toward transition metal complexes.

A. Main-Group Metal Complexes

The broader subject of the interaction of stable carbenes with main-group com-
pounds has recently been reviewed.56 Accordingly, the following discussion fo-
cuses on metallic elements of the s and p blocks. Dimeric NHC–alkali adducts have
been characterized for lithium, sodium, and potassium. For imidazolin-2-ylidenes,
alkoxy-bridged lithium dimer 20 and a lithium–cyclopentadienyl derivative 21
have been reported.57 For tetrahydropyrimid-2-ylidenes, amido-bridged dimers 22
have been characterized for lithium, sodium, and potassium.27,28 Since one of the
synthetic approaches to stable NHCs involves the deprotonation of imidazolium
cations with alkali metal bases, the interactions of alkali metal cations with NHCs
are considered to be important for understanding the solution behavior of NHCs.
Me3Si
Ar SiMe3 TMS TMS
N N Me3Si N N
O N
Li Li Li M M
O N
N N N N N
Ar TMS TMS
N
M = Li, Na, K

20 21 22
 Metal Complexes of Stable Carbenes 9

The fact that NHCs form stable compounds with beryllium, one of the hard-
est Lewis acids known and without p-electrons to “back donate,” shows the nu-
cleophilicity of these ligands. Reaction of 1,3-dimethylimidazolin-2-ylidene with
polymeric BeCl2 results in the formation of the neutral 2:1 adduct 23 or the cationic
3:1 adduct 24.58 The first NHC–alkaline earth metal complex to be isolated was
the 1:1 adduct 25 with MgEt2.59 Whereas 1,3-dimesitylimidazolin-2-ylidene re-
sults in the formation of a dimeric compound, the application of sterically more
demanding 1,3-(1-adamantyl)imidazolin-2-ylidene gives a monomeric adduct.59
Cl
N N R
N N N N N
Et
Be Be Mg
N Cl Et
Cl N Cl N N
N R

23 24 25

A variety of magnesium, calcium, strontium, and barium complexes 26–27

have been prepared starting with either the corresponding [M{N(SiMe3)2}2(thf )2]
or [(η5-C5Me5)2M].60,61 The resulting C5Me5 complexes 27 reveal different co-
ordination modes for the C5Me5 ligand depending on the metal: In the case of
Mg, one cyclopentadienyl ring is η5-bound; the other is intermediate between
η3- and η1-bound. The higher homologues, calcium and barium, feature two
η5-bound cyclopentadienyl rings. As expected, all these complexes show a non-
linear arrangement for the C5Me5-M-C5Me5 unit. With the heavier alkaline earth
metals strontium and barium, it is also possible to isolate bis(NHC) complexes
starting with [M(η5-C5Me5)2].
R
R N
N N R N
M N(SiMe ) M
3 2
N N
N(SiMe3)2
R

M = Ca, Sr, Ba M = Mg, Ca, Sr, Ba

26 27

The metal–donor bonds are predominantly ionic and become more labile for
calcium, strontium, and barium compared to beryllium and magnesium. The sol-
ubility and stability of the complexes decrease from calcium to barium. The 1:1
adducts of NHCs with BH3 or BF3 (28 and 29) are thermally stable and can be
sublimed without decomposition.62,63 This is in sharp contrast to the properties of
conventional carbenes, which rely on a pronounced metal-to-ligand back donation
and are, thus, not suited to forming adducts with electron-poor fragments such as
10 HERRMANN et al.

boron(III). Other examples for boron(III) adducts of NHCs have been reported for
BEt364 and for a borabenzene derivative resulting in adduct 30.65

N N N
BF3 BH3 B
N N N

28 29 30

NHC–group 13 metal adducts other than that for boron have been described for
aluminum, gallium, and indium (31–33).66–70

R
R N N N
MH3 MMe3 InX3
N N N
R
R

M = Al, Ga, In M = Al, Ga X = Cl, Br

31 32 33

Indium(III)–NHC complexes have been isolated in the form of their trihydrides

31 and trihalides 33. For the halides, mono and bis(NHC) adducts are formed
when InX3 (X = Br, Cl) is exposed to the respective stoichiometric amounts of the
NHC.67 For the hydrides, a substitution reaction at [InH3(NMe3)] or Li[InH4] gives
the respective compounds.68 The thermal stability of [InH3(NHC)] complexes
was increased remarkably by using 1,3-dimesitylimidazolin-2-ylidene rather than
less sterically demanding NHCs.71 It was impossible to obtain bis(NHC) com-
plexes with the IrH3 fragment, presumably as a consequence of the reduced Lewis
acidity of the InH3 moiety compared to the indium halides, which form these 2:1
adducts readily. There are fewer data known for the hydride adducts 31 of alu-
minum and gallium. But the fact that these NHC adducts—again especially with
sterically demanding NHCs—are reported to be of higher stability than adducts
with other Lewis bases supports the postulation that NHCs are characterized by
high nucleophilicity and Lewis basicity.66 In general, the thermal stabilities of the
NHC–group13-hydrides decrease from aluminum to indium. Trialkyl complexes
32 are known for aluminum and gallium.70 NHC adducts with (semi-)metals of
group 14 are known for silicon, germanium, tin, and lead.72–74 The germanium(II)
and tin(II) halides 34 and 35 are again prepared by an adduct formation starting
from the free NHC and GeI2 or SnCl2, respectively. A tin alkyl adduct is formed
by using bis(2,4,6-tri-iso-propylphenyl)tin(II) as the precursor. The structural data
for all these compounds are consistent with the observations made for other NHC
complexes: long M– C bonds suggesting single-bond character, which makes the
 Metal Complexes of Stable Carbenes 11

compounds best described as Lewis acid–Lewis base adducts.

Mes R
N N N N N
Ge Sn Pb Si
I Cl Ar
N I N Cl N Ar N N
Mes R

34 35 36 37

Plumbene–NHC complex 36 is generated by the reaction of an NHC with a

bis(aryl)-lead(II) compound.75 The NHC–silylene adduct 37 also features a long
C–Si bond with significant δ+ C Siδ− polarity.76 Pentacoordinated silicon(IV) and
tin(IV) compounds 38–40 can be generated when the precursor SiCl4, Ph2SiCl2,
Me2SiCl2, or Ph2SnCl2 is reacted with NHCs.74,77
R R R
N Cl N Cl N Cl
Ph Me Cl
M Si Si
N Cl Ph N Cl Me N Cl Cl
R R R
M = Si, Sn
38 39 40

To our knowledge no (semi-)metal adducts of stable carbenes are known for

groups 15 and 16 except 41–43.63,78,79 However, the oxidation of a 2-telluroimida-
zoline with iodine provides an interesting point of connection, effectively providing
a TeI2 adduct of a NHC.80
Mes Mes Mes
Cl N Cl N Cl N
MF5 Sb(CF3)3 As
N N N R
Cl Cl Cl
Mes Mes Mes

M = As, Sb R = Ph, C6F5

41 42 43

B. Transition Metal Complexes

Since there are many more carbene–transition-metal complexes known than

main-group adducts this chapter is organized by the synthetic methods that lead to
the complexes rather than by the metal itself. Applications of these complexes to
catalysis and materials science will be discussed in separate chapters of this article.
Exploring the Variety of Random
Documents with Different Content
 Journalism - Research Paper
Third 2024 - Laboratory

Prepared by: Researcher Jones

Date: July 28, 2025

Test 1: Statistical analysis and interpretation

Learning Objective 1: Literature review and discussion
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Learning Objective 2: Study tips and learning strategies
• Key terms and definitions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Learning Objective 3: Case studies and real-world applications
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Learning Objective 4: Problem-solving strategies and techniques
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Learning Objective 5: Critical analysis and evaluation
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Key terms and definitions
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 6: Theoretical framework and methodology
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Practical applications and examples
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Case studies and real-world applications
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Current trends and future directions
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Summary 2: Literature review and discussion
Important: Research findings and conclusions
• Research findings and conclusions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Note: Best practices and recommendations
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 12: Historical development and evolution
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 13: Practical applications and examples
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 14: Case studies and real-world applications
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Case studies and real-world applications
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 16: Study tips and learning strategies
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 17: Diagram/Chart/Graph]
Key Concept: Research findings and conclusions
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Key Concept: Historical development and evolution
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Practice Problem 19: Theoretical framework and methodology
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Abstract 3: Key terms and definitions
Example 20: Current trends and future directions
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Key Concept: Key terms and definitions
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 22: Diagram/Chart/Graph]
Important: Statistical analysis and interpretation
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Note: Historical development and evolution
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Note: Study tips and learning strategies
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 25: Comparative analysis and synthesis
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Practice Problem 26: Current trends and future directions
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Key Concept: Ethical considerations and implications
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Practice Problem 28: Learning outcomes and objectives
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 29: Best practices and recommendations
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Review 4: Key terms and definitions
Key Concept: Case studies and real-world applications
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Ethical considerations and implications
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Comparative analysis and synthesis
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Important: Theoretical framework and methodology
• Research findings and conclusions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Theoretical framework and methodology
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Example 35: Problem-solving strategies and techniques
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Practice Problem 36: Assessment criteria and rubrics
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Study tips and learning strategies
• Research findings and conclusions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 38: Diagram/Chart/Graph]
Remember: Literature review and discussion
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 39: Diagram/Chart/Graph]
Note: Literature review and discussion
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Methodology 5: Assessment criteria and rubrics
Key Concept: Statistical analysis and interpretation
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 41: Experimental procedures and results
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Fundamental concepts and principles
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 43: Diagram/Chart/Graph]
Note: Interdisciplinary approaches
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Study tips and learning strategies
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 45: Diagram/Chart/Graph]
Practice Problem 45: Case studies and real-world applications
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Assessment criteria and rubrics
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Statistical analysis and interpretation
• Research findings and conclusions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Case studies and real-world applications
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 49: Diagram/Chart/Graph]
Practice Problem 49: Key terms and definitions
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Abstract 6: Problem-solving strategies and techniques
Note: Problem-solving strategies and techniques
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 51: Diagram/Chart/Graph]
Note: Historical development and evolution
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 52: Diagram/Chart/Graph]
Definition: Theoretical framework and methodology
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 53: Diagram/Chart/Graph]
Practice Problem 53: Case studies and real-world applications
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Assessment criteria and rubrics
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Research findings and conclusions
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Best practices and recommendations
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Experimental procedures and results
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Critical analysis and evaluation
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Experimental procedures and results
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Appendix 7: Case studies and real-world applications
Example 60: Study tips and learning strategies
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Practice Problem 61: Current trends and future directions
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Research findings and conclusions
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Practice Problem 63: Critical analysis and evaluation
• Key terms and definitions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 64: Historical development and evolution
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Example 65: Assessment criteria and rubrics
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Important: Comparative analysis and synthesis
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Definition: Statistical analysis and interpretation
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Example 68: Case studies and real-world applications
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Fundamental concepts and principles
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 70: Diagram/Chart/Graph]
Practice 8: Interdisciplinary approaches
Remember: Theoretical framework and methodology
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Definition: Historical development and evolution
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Important: Critical analysis and evaluation
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 73: Diagram/Chart/Graph]
Definition: Case studies and real-world applications
• Research findings and conclusions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 74: Diagram/Chart/Graph]
Key Concept: Case studies and real-world applications
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Key Concept: Theoretical framework and methodology
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Practical applications and examples
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Remember: Research findings and conclusions
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Example 78: Research findings and conclusions
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 79: Diagram/Chart/Graph]
Example 79: Problem-solving strategies and techniques
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Part 9: Fundamental concepts and principles
Example 80: Historical development and evolution
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Remember: Interdisciplinary approaches
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Ethical considerations and implications
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Historical development and evolution
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Important: Best practices and recommendations
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Practice Problem 85: Statistical analysis and interpretation
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Learning outcomes and objectives
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 87: Diagram/Chart/Graph]
Practice Problem 87: Best practices and recommendations
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Experimental procedures and results
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Important: Critical analysis and evaluation
• Key terms and definitions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Chapter 10: Fundamental concepts and principles
Definition: Key terms and definitions
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Research findings and conclusions
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Best practices and recommendations
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Important: Interdisciplinary approaches
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 94: Diagram/Chart/Graph]
Remember: Interdisciplinary approaches
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Example 95: Study tips and learning strategies
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 96: Diagram/Chart/Graph]
Definition: Key terms and definitions
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Assessment criteria and rubrics
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 98: Diagram/Chart/Graph]
Important: Practical applications and examples
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Fundamental concepts and principles
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Section 11: Current trends and future directions
Key Concept: Current trends and future directions
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Current trends and future directions
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 102: Best practices and recommendations
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 103: Diagram/Chart/Graph]
Note: Problem-solving strategies and techniques
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Definition: Study tips and learning strategies
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Comparative analysis and synthesis
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 106: Diagram/Chart/Graph]
Important: Best practices and recommendations
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Experimental procedures and results
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Learning outcomes and objectives
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Definition: Learning outcomes and objectives
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
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