Divergent Functionalization of N-Alkyl-2-alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines.

An efficient divergent functionalization of N-alkylated ortho-alkenylanilines to substituted indoles and quinolines has been accomplished by employing rhodium-catalyzed cross-dehydrogenative coupling and silver-mediated oxidative cyclization, respectively. The developed methods tolerate various functional groups and allow the synthesis of substituted indoles and quinolines in good to excellent yield. Synthetic utility is demonstrated through conversion to an indole with antimicrobial activity and C-H bond functionalization of 2-arylquinolines. Furthermore, a plausible mechanism was proposed based on preliminary mechanistic investigations.