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Engineered C–S Bond Construction

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Abstract

Due to the versatile applications of thioethers and thioesters in organic synthesis, medicinal chemistry, the pharmaceutical industry, and materials science, recently the construction of C–S bonds has emerged as the forefront in the field of cross-coupling reactions. Enough progress has been made in this direction by using both metal catalysis and other alternative processes. A brief review of the recent developments in the area of C–S coupling reaction is described.

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Abbreviations

Ac:

Acetyl

Ar:

Aryl

BMIM:

1-Butyl-3-methylimidazolium 

Bn:

Benzyl

Bpy:

2,2′-Bipyridyl

Bu:

Butyl

cat.:

Catalytic

cod:

Cyclooctadiene

cp:

Pentamethylcyclopentadienyl

Cy:

Cyclohexyl

dba:

Dibenzylideneacetone

DCE:

Dichloroethene

DCP:

Dicumyl peroxide

DIB:

Diacetoxyiodobenzene

DMA:

N,N-dimethylacetamide

DMAP:

4-Dimethylaminopyridine

DMEDA:

N,N′-dimethylethylenediamine

DMF:

Dimethylformamide

dmg:

Dimethylglyoxime

DMSO:

Dimethyl sulfoxide

dppe:

1,2-Bis(diphenylphosphino)ethane 

DPPF:

1,1′-Bis(diphenylphosphino)ferrocene

dppp:

1,3-Bis(diphenylphosphino)propane

DTBP:

Di-tert-butyl peroxide 

dtbpy:

4,4′-Di-tert-butyl-2,2′-bipyridyl

Equiv:

Equivalent

H:

Hour

Me:

Methyl

MW:

Microwave

NMP:

N-Methylpyrrolidone

PEG:

Polyethylene glycol 

Phen:

Phenanthroline 

Ph:

Phenyl

Pr:

Propyl

Psi:

Pound per square inch

TBAB:

Tetrabutylammonium bromide

TBAI:

Tetrabutylammonium iodide

TBAOH:

Tetrabutylammonium hydroxide

TBHP:

tert-Butyl hydroperoxide

TFA:

Trifluoroacetic acid

Tf:

Trifluoromethanesulfonyl

THF:

Tetrahydrofuran

TMEDA:

N,N,N′,N′ Tetramethylethylenediamine

RuPhos:

2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl

SPhos:

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

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Acknowledgements

This work was financially supported by the Ministry of Science and Technology, Taiwan (MOST 106-2113-M-005-001-), National Chung Hsing University and the “Innovation and Development Center of Sustainable Agriculture” from The Featured Areas Research Center Program within the framework of the Higher Education Sprout Project by the Ministry of Education (MOE) in Taiwan.

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Authors and Affiliations

  1. Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan

    Chin-Fa Lee & R. Sidick Basha

  2. Research Center for Sustainable Energy and Nanotechnology (NCHU), Taichung, Taiwan

    Chin-Fa Lee

  3. Innovation and Development Center of Sustainable Agriculture (NCHU), Taichung, Taiwan

    Chin-Fa Lee

  4. Centre of Advance Study, Department of Chemistry, University of Rajasthan, Jaipur, Rajasthan, 302004, India

    Satpal Singh Badsara

Authors
  1. Chin-Fa Lee
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  2. R. Sidick Basha
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  3. Satpal Singh Badsara
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Correspondence to Chin-Fa Lee.

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This article is part of the Topical Collection “Sulfur Chemistry”; edited by Xuefeng Jiang.

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Lee, CF., Basha, R.S. & Badsara, S.S. Engineered C–S Bond Construction. Top Curr Chem (Z) 376, 25 (2018). https://doi.org/10.1007/s41061-018-0203-6

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