Photo-induced stereo- and regiospecific sulfonylation of C–C multiple bonds exploiting the dual reactivity of sulfonium iodate(i) species

Abstract

Vinyl sulfones are privileged motifs for assembling prevalent biologically active molecules and represent “gateway functional groups” in medicinal chemistry and drug discovery. Augmented on our focus research toward bisfunctionalization of...

Photocatalytic iodosulfonylation of internal alkynes under green conditions

“…42 Zhang et al reported the violet (400 nm) light-induced synthesis of (E)-β-phenoxyvinylsulfones via an EDA complex-mediated radical reaction. 43 Using visible light, we, 44 Mutra et al, 45 and Gurawa et al 46 have recently shown that the photoinduced addition of RSO 2 I to internal alkynes in acetonitrile occurs with high yields and regio-and stereoselectivity. Such a reaction would represent in principle an ideal atom-saving process.…”

“…Using visible light, we, 44 Mutra et al , 45 and Gurawa et al 46 have recently shown that the photoinduced addition of RSO 2 I to internal alkynes in acetonitrile occurs with high yields and regio- and stereoselectivity. Such a reaction would represent in principle an ideal atom-saving process.…”

Recent trends in the synthesis and applications of β-iodovinyl sulfones: a decade of progress

“…Very recently, Kashyap and co-workers 26 presented the visible-light irradiated vicinal iodosulfonylation of alkynes 1 using sodium sulfinate salts 2 and sulfonium bis(acetoxy)iodate( i ) [Me 3 SI(OAc) 2 ] to synthesize the stereospecific ( E )-β-iodovinyl sulfones 3 (Scheme 9). Herein, Me 3 SI(OAc) 2 has dual reactivity as an iodine source as well as an oxidant.…”

Recent Advancements in Metal‐Catalyst‐Free Multicomponent Radical Sulfonylation of Alkynes

“…In 2023, Kashyap's group proposed a photocatalytic (E)-stereospecific direct iodosulfonylation of alkynes using sulfonium iodate species (Scheme 21). [31] In this reaction, sulfonium bis-(acetoxy) iodate (I) [Me 3 SI(OAc) 2 ] (57) would generate the sulfonyl iodide (ArSO 2 -I) in the presence of sodium aryl sulfinate (ArSO 2 -Na, 46), followed by visible lightinduced homolysis of ArSO 2 -I, which leads to the regiospecific sulfonyl-iodination reaction with alkynes. In control experiments with styrene, the isolation of the β-iodosulfone confirmed a two-step sequential process of regioselective radical sulfonyliodination of an olefinic moiety under visible-light irradiation and subsequent β-elimination.…”