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Xie, Dong‐Tai; Chen, Hong‐Lei; Wei, Dian; Wei, Bang‐Yi; Li, Zheng‐Hu; Zhang, Jian‐Wu; Yu, Wei; Han, Bing
Angewandte Chemie International Edition, July 25, 2022, Letnik: 61, Številka: 30Journal Article
A novel distal radical rearrangement of alkoxyphosphine is developed for the first time and applied to the regioselective radical fluoroalkylphosphorylation of unactivated olefins. By employing a one‐pot two‐step reaction of (bis)homoallylic alcohols, organophosphine chlorides, and fluoroalkyl iodides under CFL (compact fluorescence light) irradiation, a series of fluoroalkylphosphorylated alkyl iodides and alcohols are easily synthesized by regiospecific installing a phosphonyl onto the inner carbon of terminal olefins and further iodination/hydroxylation. Mechanism studies reveal that the migration undergoes a distinctive radical cyclization/β‐scission on the lone electron pair of phosphorus, resulting in C−P bond formation and C−O bond cleavage. A regioselective radical fluoroalkylphosphorylation of unactivated alkenes is developed by a one‐pot reaction of (bis)homoallylic alcohols, phosphine chlorides, and fluoroalkyl iodides under compact fluorescence light (CFL) irradiation. This protocol employs a novel radical rearrangement of alkoxyphosphine to achieve the unusual installing of a phosphoryl in the inner side of the terminal olefins by the dehydroxylative trifunctionalization of (bis)homoallylic alcohols.
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