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

Green Chemistry Pub Date: 2020-05-06 DOI: 10.1039/D0GC00687D

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
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