Abstract

A rhodium-catalyzed oxidative C-H/N-H dehydrogenative [3 + 2] annulation strategy has been reported between anilines and N-allylbenzimidazole for the synthesis of 2-methylindole scaffolds. An N-allylbenzimidazole has been used as a 2C synthon for the synthesis of indole, and more importantly, this transformation involves the cleavage of the thermodynamically stable C-N bond of allylamine. Detailed mechanistic studies have been performed and a key intermediate was detected in HRMS. This transformation proceeds through a cascade of C(sp2)-H allylation followed by intramolecular cyclization.

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