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Pushing Boundaries: What’s Next in Metal-Free C–H Functionalization for Sulfenylation?

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Abstract

The synthesis of thioether derivatives has been explored widely due to the potential application of these derivatives in medicinal chemistry, pharmaceutical industry and material chemistry. Within this context, there has been an increasing demand for the environmentally benign construction of C–S bonds via C–H functionalization under metal-free conditions. In the present article, we highlight recent developments in metal-free sulfenylation that have occurred in the past three years. The synthesis of organosulfur compounds via a metal-free approach using a variety of sulfur sources, including thiophenols, disulfides, sulfonyl hydrazides, sulfonyl chlorides, elemental sulfur and sulfinates, is discussed. Non-conventional strategies, which refer to the development of thioether derivatives under visible light and electrochemically mediated conditions, are also discussed. The key advantages of the reviewed methodologies include broad substrate scope and high reaction yields under environmentally benign conditions. This comprehensive review will provide chemists with a synthetic tool that will facilitate further development in this field.

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Abbreviations

o-DCB:

o-Dichlorobenzene

DCE:

Dichloroethane

DMA:

Dimethyl acetamide

DMF:

Dimethyl formamide

DMSO:

Dimethyl sulfoxide

DPDME:

Dimethyl dipropylene glycol

GO:

Graphene oxide

LEDs:

Light-emitting diodes

NIS:

N–Iodosuccinimide

NMP:

N-Methyl-2-pyrrolidone

PIDA:

Diacetoxyiodobenzene

PIFA:

Phenyliodine bis(trifluoroacetate)

RT:

Room temperature

TBAI:

TetraButyl ammonium iodide

TBHP:

Tert-Butylhydroperoxide

THF:

Tetrahydrofuran

TMAI:

Tetramethyl ammonium iodide

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Acknowledgements

Payal Rani is grateful to UGC for offering financial aid through Senior Research Fellowship (SRF) [UGC Reference No. 269/(CSIR-UGC NET JRF DEC.-2017)]. Sandhya is thankful to CCSHAU for providing research fellowship.

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  1. Department of Chemistry, College of Basic Sciences & Humanities, Chaudhary Charan Singh Haryana Agricultural University (CCS HAU), Hisar, Haryana, 125004, India

    Payal Rani, Sandhya Chahal, Rajvir Singh & Jayant Sindhu

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Rani, P., Chahal, S., Singh, R. et al. Pushing Boundaries: What’s Next in Metal-Free C–H Functionalization for Sulfenylation?. Top Curr Chem (Z) 382, 13 (2024). https://doi.org/10.1007/s41061-024-00460-1

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