Issue 12, 2020

Electrochemical oxidative C(sp3)–H azolation of lactams under mild conditions

Abstract

Lactam-containing structural compounds are ubiquitous in drugs and biomolecules. An electrochemical oxidative direct C(sp3)–H azolation of lactams has been reported under metal catalyst-free and external chemical oxidant-free conditions. This electrochemical C(sp3)–H/N–H coupling is characterized by its broad substrate scope of azoles and lactams under mild conditions at room temperature. Mechanistic studies suggested that the reaction possibly involves a radical process. Moreover, the site selectivity can be explained by DFT calculations. More meaningfully, a gram-scale synthesis method of flow electrochemistry was employed to show the scaled-up applicability of this transformation.

Graphical abstract: Electrochemical oxidative C(sp3)–H azolation of lactams under mild conditions

Supplementary files

Article information

Article type
Communication
Submitted
26 Feb 2020
Accepted
30 Apr 2020
First published
06 May 2020

Green Chem., 2020,22, 3742-3747

Electrochemical oxidative C(sp3)–H azolation of lactams under mild conditions

Z. Wan, D. Wang, Z. Yang, H. Zhang, S. Wang and A. Lei, Green Chem., 2020, 22, 3742 DOI: 10.1039/D0GC00687D

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