Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C–C bond cleavage. Issue 4 (17th December 2019)

• Record Type: Journal Article
• Authors: Xu, Zhongnan; Huang, Zhixing; Li, Yueheng; Kuniyil, Rositha; Zhang, Chao; Ackermann, Lutz; Ruan, Zhixiong
• Is Part Of: Green chemistry. Volume 22:Issue 4(2020)
• Page Start: 1099
• Page End: 1104
• Publication Date: 2019-12-17
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c9gc03901e
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Expanding ring under green electricity: The electrosynthetic approach enabled atom-economical synthesis of challenging medium-sized lactams through a unique remote amidyl migration under exceedingly mild, transition metal- and oxidant-free conditions. Abstract : A catalyst-free, direct electrochemical synthesis of synthetically challenging medium-sized lactams through C–C bond cleavage has been developed. In contrast to previous typical amidyl radical cyclization, this electrosynthetic approach enabled step-economical ring expansion through a unique remote amidyl migration under mild, metal- and external-oxidant-free conditions in a simple undivided cell. The strategy features unparalleled broad substrate scope with all ring sizes of (hetero)aryl-fused 8–11-membered rings and hetero atom-tethered rings, high yields, and good functional group tolerance. Our experimental and computational findings provided strong support for a SET-based reaction manifold.