Photoredox/Nickel Dual-Catalyzed Regioselective Allylic Arylations of Allyl Trifluoroborates with Aryl Halides

Org Lett. 2023 May 12;25(18):3319-3324. doi: 10.1021/acs.orglett.3c01147. Epub 2023 Apr 27.

Abstract

An efficient photoredox/nickel dual-catalyzed coupling of allyl trifluoroborates with aryl halides has been developed, which provides an attractive route to diverse-substituted allylic benzenes. The method offers several advantages, such as high efficiency and regioselectivity, mild reaction conditions, wide substrate scope, and functional group compatibility. Mechanistic studies suggest that a π-allyl nickel(III) intermediate generated via the addition of an allyl radical to nickel species is possibly formed as a key reaction intermediate.