Divergent Functionalization of N‐Alkyl‐2‐alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines. Issue 17 (10th June 2018)

• Record Type: Journal Article
• Authors: Ghorai, Jayanta; Reddy, Angula Chandra Shekar; Anbarasan, Pazhamalai
• Is Part Of: Chemistry, an Asian journal. Volume 13:Issue 17(2018)
• Page Start: 2499
• Page End: 2504
• Publication Date: 2018-06-10
• Subjects: homogeneous catalysis -- reaction mechanisms -- rhodium -- ring expansion -- silver; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201800441
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: 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. Abstract : Path to the ring : 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 (see scheme).