Selective C−N Bond Cleavage of N‐Acylisatins: Towards High Performance Acylation/Arylation/Transamination Reagents

Abstract

AbstractNew multipurpose arylation/acylation/transamination reagents, N‐acylisatins, have been developed by selective ‘inside‐outside’ C−N bond cleavage under different catalytic conditions. As activated amides, N‐acylisatins undergo Rh‐catalyzed C−H arylation and Pd‐catalyzed acylation by cleavage outside the C−N bond, and the desired biaryls and diaryl ketones were obtained in good to excellent yields. Generally, the combination of N‐acylisatins with amines leads to a ring‐opening reaction and formation of transamination products in a predictable manner through inside C−N bond cleavage. Interestingly, treatment of N‐acylisatins with amines lead to unexpected outer‐ring transamination products when CsF is added, which shows that CsF can favor the outside C−N bond cleavage path. Notably, this work presents a new strategy for multiple chemical transformations of a single amide to achieve various products by selective C−N bond cleavage.magnified image