Organometallic Approaches to Carbon–Sulfur Bond Formation

Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 31)

Abstract

The transition metal mediated synthesis of carbon–sulfur (C–S) bonds is possible with a variety of simple and tailored metal complexes. This chapter serves to illustrate developments over the last decade involving the catalytic synthesis of C–S bonds with various transition metals, focusing on cross-coupling reactions and addition to π-bonds.

Graphical Abstract

Keywords

Carbon–sulfur Cross-coupling Catalysis Bond activation 

Abbreviations

%

Mol %

Acac

Acetylacetonate

AcOH

Acetic acid

atm

Atmosphere

BINAM

1,1′-binaphthyl-2,2′-diamine

±BINAP

Racemic 2,2′-bis(diphenylphosphino)-1,1′-binapthyl

[bmim][OTf]

1-butyl-3-methylimidazolium triflate

Bn

Benzyl

Bu

Butyl

C–S

Carbon–sulfur

CH3CN

Acetonitrile

cod

Cyclooctadiene

Conv.

Conversion

COX-2

Cyclooxygenase-2

CuI–bipy

Copper(I) iodide–bipyridine complex

CuMeSal

Copper(I) 3-methylsalicylate

Cy

Cyclohexyl

DIPEA

Diisopropylethyl amine

DCE

1,2-Dichloroethane

DIPPF

1,1′-Bis(diisopropylphosphino)ferrocene

DME

Dimethoxyethane

DMAD

Dimethylaceylene dicarboxylate

DMEDA

Dimethylethylenediamine

DMF

Dimethylformamide

DMSO

Dimethyl sulfoixde

DPEphos

Oxydi-2,1-phenylene)bis(diphenylphosphine)

dppBz

1,2-Bis(diphenylphosphino)benzene

dppe

1,2-Bis(diphenylphosphino)ethane

dppf

1,1′-Bis(diphenylphosphino)ferrocene

R-DTBM-Segphos

[(4R)-(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine]

ee

Enantiomeric excess

EtOH

Ethanol

HMPA

Hexamethylphosphoramide

Imes

1,3-bis(2,4,6-trimethylphenyl)-2,3-dihydro-1H-imidazaol-2-ylidene

i-PrOH

Isopropanol or 2-methylpropanol

Josiphos

(R)-1-[(SP)-2-(Di-tert-butylphosphino)ferrocenyl]ethylbis(2-methylphenyl)phosphine

LiHMDS

Lithium bis(trimethylsilyl)amide

m-

Meta substitution

Me

Methyl

MLn

Transition metal complex

n-BuLi

n-Butyllithium

t-BuONa

Sodium tert butoxide

NHC

N-Heterocyclic carbine

o-

Ortho substitution

OAc

Acetate

OMs

Methanesulfonate

p-

Para substitution

P2–Et

1-Ethyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ5-catenadi(phosphazene)

Pd2dba3

Tris(dibenzylideneacetone)dipalladium(0)

Ph

Phenyl

PhCH3

Toluene

PhH

Benzene

PhCl

Chlorobenzene

RhCl(PPh3)3

Wilkinson’s catalyst

SPhos

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

t-Bu

Tert-butyl

t-BuOH

Tert-Butanol

t-BuOK

Potassium tert butoxide

THF

Tetrahydrofuran

TMEDA

Tetramethylethylenediamine

Tp*

hydrotris(3,5-dimethylpyrazolyl)-borate

Xantphos

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

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© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of British ColumbiaVancouverCanada

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