Visible-Light-Induced 1,4-Hydroxysulfonylation of Vinyl Enynes with Sulfonyl Chlorides: The Bridge of Chloride Linking Water and Enynes
Chengyun Zhang, Jie Zhu, Su‐Hang Cui, Xiaoyu Xie, Xiaodong Wang, Lei Wu
Abstract
A novel visible-light-induced 1,4-hydroxysulfonylation of vinyl enynes with sulfonyl chlorides has been established, providing a highly efficient protocol to access multisubstituted sulfonyl allenic alcohols. Control experiments and mechanistic studies disclose that the target products result from sequential reactions of hydroxyl and tosyl radicals, among which chloride anion plays a key role to generate the requisite •OH, thus bridging water and enynes. Moreover, the vinyl pendant is believed to decisively affect the site-selectivity of hydroxyl radical.
Topics & Concepts
ChemistrySulfonylVinyl chlorideRadicalChlorideTosylCombinatorial chemistryOrganic chemistryAlkylCopolymerPolymerSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods