Remote C(sp3)–H activation: palladium-catalyzed intermolecular arylation and alkynylation with organolithiums and terminal alkynes

Abstract

A 1,4-palladium shift is regarded as one of the solutions towards the challenging remote C(sp³)–H activation. Herein, we report two efficient remote C(sp³)–H activation protocols involving palladium-catalyzed C(sp³)–C(sp²) and C(sp³)–C(sp) cross-coupling with aryllithium reagents and terminal alkynes as key coupling partners, respectively. More than 50 examples with acceptable to high yields, good functional group tolerance, and high regioselectivities are presented. The practicality of the reaction is demonstrated in a gram-scale manner.