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Three‐Component Reaction of Potassium Alkyltrifluoroborates, Sulfur Dioxide and Allylic Bromides under Visible‐Light Irradiation
Author(s) -
Ye Shengqing,
Li Xiaofang,
Xie Wenlin,
Wu Jie
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900172
Subject(s) - chemistry , allylic rearrangement , sulfur dioxide , sulfone , photochemistry , alkyl , sulfur , photocatalysis , irradiation , potassium , radical , visible spectrum , potassium perchlorate , catalysis , organic chemistry , physics , optoelectronics , nuclear physics
Abstract Diverse allylic sulfones are generated through a three‐component reaction of potassium alkyltrifluoroborates, sulfur dioxide and allylic bromides in the presence of 9‐mesityl‐10‐methyl acridinium perchlorate under visible light irradiation at room temperature. This transformation proceeds efficiently, and a broad reaction scope is demonstrated with good functional groups tolerance. This reaction is initiated by the treatment of potassium alkyltrifluoroborate under visible‐light irradiation in the presence of a photocatalyst, leading to alkyl radical. This alkyl radical intermediate is trapped by sulfur dioxide to provide alkylsulfonyl radical, which then undergoes further transformation to afford the corresponding allylic sulfone.