Issue 22, 2021

Metal-free electrochemical [3 + 2] heteroannulation of anilines with pyridines enabled by dual C–H radical aminations

Abstract

An unprecedented metal-/external-oxidant-free electrochemical intermolecular [3 + 2] heteroannulation of anilines with electron-deficient pyridines enabled by dual C–H radical aminations for producing functionally diverse benzo[4,5]imidazo[1,2-a]pyridines is described. The site-selectivity of aminations of aryl C(sp2)–H bonds relies on the electronic effect of two reaction partners: each contributed two reactive sites (a C(sp2)–H bond and a nitrogen atom-based functional group) and the electron-withdrawing groups at the 4 position of the pyridine ring are crucial. Mechanistic studies show that this method sequence consists of the generation of the nitrogen-centered radical (NCR) and the pyridine radical anion, radical coupling and dual C–N aminations.

Graphical abstract: Metal-free electrochemical [3 + 2] heteroannulation of anilines with pyridines enabled by dual C–H radical aminations

Supplementary files

Article information

Article type
Paper
Submitted
13 Aug 2021
Accepted
12 Oct 2021
First published
12 Oct 2021

Green Chem., 2021,23, 9024-9029

Metal-free electrochemical [3 + 2] heteroannulation of anilines with pyridines enabled by dual C–H radical aminations

M. Luo, X. Ouyang, Y. Zhu, Y. Li and J. Li, Green Chem., 2021, 23, 9024 DOI: 10.1039/D1GC02922C

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