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Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C–C bond cleavage

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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.

Graphical abstract: Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C–C bond cleavage

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Article information


Submitted
12 Nov 2019
Accepted
06 Dec 2019
First published
11 Dec 2019

Green Chem., 2020, Advance Article
Article type
Communication

Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C–C bond cleavage

Z. Xu, Z. Huang, Y. Li, R. Kuniyil, C. Zhang, L. Ackermann and Z. Ruan, Green Chem., 2020, Advance Article , DOI: 10.1039/C9GC03901E

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