Reactions of alkynes with C–S bond formation: recent developments

Abstract

Alkynes are important in organic synthesis. This review mainly focuses on recent advances (2013–2023) on alkynes with C–S bond formation, based on more than 30 types of sulfur reagents. The reactions of alkynes with various sulfur-containing compounds including RSSR (disulfides), RSH (thiols), S₈ (elemental sulphur), alkynyl thioethers, RSCN, AgSCF₃, K₂S, Na₂S, dithiane, RSCl, NFSI, RNCS, EtOCS₂K, thiocarbamate, RSONH₂, thiourea, sulfoxide, RSO₂N₃, CS₂, RSO₂NH₂, RSO₂NHNH₂, RSO₂Cl, RSO₂Oar, RSO₂SR′, DABCO·(SO₂)₂, Na₂S₂O₅, K₂S₂O₅, RSO₂H, RSO₂Na and related compounds are discussed. Diverse mechanisms such as radical, electrophilic/nucleophilic addition, rearrangement, C–C bond cleavage, and CuAAC are discussed. The content is organized by substrates and reactivity patterns. We hope it will help in future research in this area.