Photocatalytic Heck-type coupling reactions of alkyl chlorides mediated by halide-exchange of CsPbBr3 nanocrystals

Abstract

Despite the significant synthetic potential and broad applicability of alkyl chlorides, their application in Heck-type coupling reactions remains a substantial challenge due to the high bond dissociation energy and low reduction potential of the C(sp³)–Cl bond. Herein, we report a facile photocatalytic strategy for Heck-type coupling of alkyl chlorides with alkenes using CsPbBr₃ nanocrystals (NCs) as a heterogeneous photocatalyst. The success of this transformation hinges on halide exchange between the alkyl chloride and CsPbBr₃ NCs that ensures the cleavage of the C(sp³)–Cl bond via an inner-sphere electron transfer pathway, which bypasses the limitations of conventional methods.