Visible-Light-Promoted Regioselective 1,3-Fluoroallylation of gem-Difluorocyclopropanes

• DOI: 10.1021/acs.orglett.0c03268
• Publication Date: 2020-10-28T20:09:15Z
• Authors: Haidong Liu; Yi Li; Ding-Xing Wang; Meng-Meng Sun; Chao Feng
• Keywords: Visible spectrum

A strategically novel protocol for ring-opening functionalization of aryl gem-difluorocyclopropanes (F2CPs), which allows an expedient construction CF3-containing architectures via visible-light-promoted F-nucleophilic attack manifold, was disclosed. Single electron oxidation F2CPs ascribed as the critical step success this transformation by prompting attack, well ensuing C–C bond scission. The observed intriguing regioselectivity fluoroincorporation in reaction rationalized invoking cation-stabilization property gem-difluorine substituents and also thermodynamic gains acquired from forming CF3 functionality. By using cost-effective fluorination reagent readily available substrates, a broad collection structurally diversified α-allyl-β-trifluoromethyl ethylbenzene derivatives could be obtained generally good yields. Further mechanistic investigations proved engagement benzylic radical intermediate transformation.