Photoredox-Catalyzed Selective α-Scission of PR<sub>3</sub>–OH Radicals to Access Hydroalkylation of Alkenes
Zhenzhen Xie, Zi‐Hao Liao, Yu Zheng, Chu‐Ping Yuan, Jianping Guan, Mingzhi Li, Ke-Yi Deng, Hao‐Yue Xiang, Kai Chen, Hua Yang
Abstract
Photoinduced generation of phosphoranyl radicals offers a versatile strategy to access a variety of synthetically valuable radicals. A long-standing challenge remains in the regulation of phosphoranyl radical to undergo α-scission pathway, although the β-scission mode has been intensively studied. We herein developed an unprecedented protocol for selective α-scission of the P(OH)R 3 radical intermediate under photocatalytic conditions. This efficient P–C bond cleavage via α-scission of the P(OH)R 3 radicals has been successfully utilized in the alkylation/fluoroalkylation of alkenes.
Topics & Concepts
RadicalBond cleavageChemistryAlkylationCatalysisCleavage (geology)PhotochemistryPhotoredox catalysisBeta scissionCombinatorial chemistryPhotocatalysisOrganic chemistryRadical substitutionEngineeringFracture (geology)Geotechnical engineeringRadical Photochemical ReactionsFluorine in Organic ChemistrySulfur-Based Synthesis Techniques