A general rhodium-catalyzed regioselective C–H functionalization: accessing heteroarylated and alkenylated arenes

Abstract

Herein, an efficient and general rhodium-catalyzed C–H heteroarylation and alkenylation of pyridotriazoles and ortho-aryl heterocycles with iodonium ylides is reported. This strategy enables the synthesis of a wide array of heteroarylated and alkenylated heterocycles and arenes under mild reaction conditions. The triazole moiety in pyridotriazoles serves exclusively as an intrinsic directing group, showcasing distinct reactivity compared to previous reports. In addition, this transformation accommodates various N-containing heterocycles and oximes as directing groups, highlighting its versatility for heterocycles and arenes functionalization. This protocol exhibits broad substrate scope, good functional group tolerance, operational simplicity, air compatibility, and scalability with low catalyst loading. Moreover, a low kinetic isotope effect value indicates C–H bond cleavage is unlikely to be the rate-determining factor.