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Rhodium Catalysts for C–S Bond Formation

  • Andrea Di Giuseppe
  • Ricardo Castarlenas
  • Luis A. OroEmail author
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 61)

Abstract

Sulfur-containing molecules are commonly found in chemical biology, organic synthesis, and materials chemistry. The preparation of these compounds through traditional methods usually required harsh reaction conditions. The use of transition-metal-based catalysts has allowed the development of more efficient and sustainable synthetic processes. Rhodium-catalyzed C–S bond formation through the reaction between sulfur sources such as S8, thiols, or disulfides with organic substrates such as alkynes, allenes, and aryl/alkyl halides is one of the most important methods in the synthesis of thioethers. Here, we summarize recent efforts in the reactions of cross coupling, C–H activation, metathesis, thiolation, carbothiolation, and hydrothiolation for the C–S bond formation catalyzed by rhodium complexes, particularly highlighting the synthetic and mechanistic aspects.

Keywords

Alkynes Allenes Carbothiolation C–H activation Cross coupling Halides Hydrothiolation Thioethers Thiolation 

Abbreviations

(S)-BIPHANE

(R,R)-1,2-Bis[(R)-4,5-dihydro-3H-binaphtho(1,2-c:2′,1′-e)phosphepino]benzene

AMLA

Ambiphilic metal ligand activation

ArF

3,5-(CF3)2C6H3

Bz

Benzyl

CMD

Concerted metalation deprotonation

Cod

Cyclooctadiene

Coe

Cyclooctene

Cp*

Pentamethylcyclopentadienyl

DCE

Dichloroethane

DDQ

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DMA

Dimethylacetamide

DMF

Dimethylformamide

DMSO

Dimethylsulfoxide

DPEPhos

Bis[(2-diphenylphosphino)phenyl] ether

Dppb

1,4-Bis(diphenylphosphino)butane

dppBz

1,2-Bis(diphenylphosphino)benzene

Dppe

1,2-Bis(diphenylphosphino)ethane

dppf

1,1′-Ferrocenediyl-bis(diphenylphosphine)

Dppp

1,3-Bis(diphenylphosphino)propane

Dpppe

1,5-Bis(diphenylphosphino)pentane

e.e.

Enantiomeric excess

IPr

1,3-Bis-(2,6-diisopropylphenyl)imidazol-2-carbene

Nbd

2,5-Norbornadiene

OAc

Acetate

OtBu

tert-Butoxide

OTf

Triflate

r.t.

Room temperature

tAmOH

2-Methyl-2-butanol

THF

Tetrahydrofuran

Tp

Hydrotris(1-pyrazolyl)borate

Tp*

Hydrotris(3,5-dimethylpyrazol-1-yl)borate

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Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  • Andrea Di Giuseppe
    • 1
  • Ricardo Castarlenas
    • 1
  • Luis A. Oro
    • 1
    Email author
  1. 1.Departamento Química Inorgánica – ISQCHUniversidad de Zaragoza – CSICZaragozaSpain

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