Rh-Catalyzed Base-Free Decarbonylative Borylation of Twisted Amides
Fusheng Bie, Xuejing Liu, Yijun Shi, Han Cao, Ying Han, Michal Szostak, Chengwei Liu
Abstract
We report the rhodium-catalyzed base-free decarbonylative borylation of twisted amides. The synthesis of versatile arylboronate esters from aryl twisted amides is achieved via decarbonylative rhodium(I) catalysis and highly selective N-C(O) insertion. The method is notable for a very practical, additive-free Rh(I) catalyst system. The method shows broad functional group tolerance and excellent substrate scope, including site-selective decarbonylative borylation/Heck cross-coupling via divergent N-C/C-Br cleavage and late-stage pharmaceutical borylation.
Topics & Concepts
BorylationRhodiumCatalysisChemistryArylCombinatorial chemistrySubstrate (aquarium)StereochemistryOrganic chemistryBiologyEcologyAlkylCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistryAdvanced Synthetic Organic Chemistry