Distal meta-C-H functionalization of α-substituted cinnamates.

Abstract

Development of a novel strategy for the palladium-catalyzed selective meta-C-H activation of α-substituted cinnamates and their heterocyclic analogues with various alkenes using nitrile as a directing group (DG) has been described. Importantly, we introduced naphthoquinone, benzoquinones, maleimides and sulfolene as coupling partners in the meta-C-H activation reaction for the first time. Notably, allylation, acetoxylation and cyanation were also achieved through distal meta-C-H functionalization. This novel protocol also includes the coupling of various olefin-tethered bioactive molecules with high selectivity.