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Visible Light-Induced Highly Regioselective and Stereoselective Oxysulfonylation of Alkynes for the Synthesis of (<i>E</i>)-β-Phenoxy Vinylsulfones

Wenjiao Xie, Pengju Ma, Yujun Zhang, Long‐Yi Xi, Sheng‐Qi Qiu, Xuan Huang, Bo Yang, Yuan Gao, Junmin Zhang

2022Organic Letters21 citationsDOI

Abstract

A highly efficient visible light-induced regioselective and stereoselective oxysulfonylation of alkynes with arylsulfonate phenol esters has been developed. This photocatalyst- and metal-free method proceeds smoothly under very mild conditions and exhibits a broad substrate scope, providing (E)-β-phenoxy vinylsulfones in moderate to excellent yields. Mechanistic studies indicated the involvement of an electron donor–acceptor complex-mediated radical process.

Topics & Concepts

RegioselectivityChemistryStereoselectivitySubstrate (aquarium)Visible spectrumPhenolAcceptorCombinatorial chemistryPhotochemistryPhotocatalysisCatalysisOrganic chemistryPhysicsOceanographyGeologyOptoelectronicsCondensed matter physicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsChemical Synthesis and Reactions
Visible Light-Induced Highly Regioselective and Stereoselective Oxysulfonylation of Alkynes for the Synthesis of (<i>E</i>)-β-Phenoxy Vinylsulfones | Litcius