Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C–H Borylation/N–C(O) Activation
Pengcheng Gao, Michal Szostak
Abstract
Herein, we demonstrate that amides can be readily coupled with nonactivated arenes via sequential Ir-catalyzed C-H borylation/N-C(O) activation. This methodology provides facile access to biaryl ketones and biaryls by the sterically controlled Ir-catalyzed C-H borylation and divergent acyl and decarbonylative amide N-C(O) and C-C activation. The methodology diverts the traditional acylation and arylation regioselectivity, allowing us to directly utilize readily available arenes and amides to produce valuable ketone and biaryl motifs.
Topics & Concepts
BorylationChemistrySteric effectsAmideRegioselectivityCatalysisAcylationArylKetoneAlleneCombinatorial chemistryStereochemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAdvanced Synthetic Organic Chemistry