Photocatalytic radical defluoroalkylation of unactivated alkenes via distal heteroaryl ipso-migration

Xin Yuan, Kai Qiang Zhuang, Yu Sheng Cui, Long Zhou Qin, Qi Sun, Xiu Duan, Lin Chen, Ning Zhu, Guigen Li, Jiang Kai Qiu, Kai Guo

Research output: Contribution to journalArticlepeer-review

Abstract

Currently, the selective activation of C(sp3)–F bonds and C–C bonds constitute one of the most widely used procedures for the synthesis of high-value products that range from pharmaceuticals to agrochemical applications. While numerous examples of these two methods have been reported in their respective fields, the processes which merge the activation of both single C(sp3)-F bonds and C–C bonds in one step still remain elusive. Here, we demonstrate the controllable defluoroalkylation–distal functionalization of trifluoromethylarenes with unactivated alkenes via distal heteroaryl migration. This is proposed to proceed via tandem C(sp3)–F and C–C bond cleavage using visible-light photoredox catalysis combined with Lewis acid activation. This strategy provides facile and flexible access to multiply functionalized α,α-difluorobenzylic ketones in useful yields (up to 88%) under mild conditions. The products can be further transformed into other valuable compounds, demonstrating the method’s utility.

Original languageEnglish
Article number98
JournalCommunications Chemistry
Volume3
Issue number1
DOIs
StatePublished - Dec 1 2020

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