Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization

Abstract

The past decade has witnessed significant advancements in the highly selective dichalcogenation (chalcogen = S, Se, Te) reactions of unsaturated substrates for the synthesis of dichalcogen compounds. The present review...

Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds

“…Addition reactions, especially via double functionalization of unsaturated compounds, have also been broadly applied for the synthesis of chalcogen-bearing compounds. 25,48–56 However, complicated chemo-, regio- and stereoselective issues exist under certain circumstances. Over the past two decades, the direct chalcogenation of C–H bonds has evolved as a straightforward, atom- and step-economical method for the preparation of chalcogenated compounds including organyl sulfides, selenides, sulfones, trifluoromethylthioethers, thiocyanates and selenocyanates.…”

Photoinduced Regioselective Sulfonylsulfination of Alkenes

“…Organosulfur compounds are of fundamental significance in modern synthetic and biological chemistry, especially sulfoxides, sulfones, sultines, and sultones, and play a pivotal role in the pharmaceutical, agrochemical, functional materials, and petrochemical industries. They are prominent structural motifs in numerous natural products, bioactive molecules, and pharmaceuticals, and provide crucial intermediates in organic synthesis. − Among the various hitherto developed organosulfur molecules, the structural motif of a two-carbon unit with a sulfone and sultone/sulfinate (sultine analogue) on each carbon has attracted extensive attention, because these frameworks have shown unique chemical and biological properties such as agrochemical fungicides, protease inhibitors, and materials (Figure a). − As such, the development of efficient methods that expand the available C2-linked 1,2-bis-sulfuratom components is of high demand, − and many elegant progress has been established in 1,2-dichalcogenation of carbon–carbon double bond based on visible-light photoredox catalysis, Lewis acid catalysis, and transition metal-catalyzed cross-coupling reactions by Maies, Wu, Jiang, Zhu, Wang, Bi, and others; however, their applications to the synthesis of dichalcogenated molecules typically involve disulfonylation, disulfenylation, thiosulfonylation, and sulfinylsulfonylation with prefunctionalized disulfur transfer reagents (Figure b).…”

Photocatalytic iodosulfonylation of internal alkynes under green conditions

“…Methods for creating carbon–heteroatom bonds, including C–S bonds, are in high demand in modern organic chemistry. 1–10 Sulfur-containing compounds are widely used as catalysts, 11,12 reagents and synthetic intermediates, 13–19 as well as for the preparation of biologically active compounds 20 and functional materials. 21,22…”