Issue 7, 2023

Electrochemical dual α,β-C(sp3)–H functionalization of cyclic N-aryl amines

Abstract

Herein, a straightforward and efficient route for the construction of dual α,β-C(sp3)–H functionalized cyclic N-aryl amines using a combination of electrocatalysis and iron catalysis is disclosed. This method is achieved by multiple single electron oxidations and is carried out in an operationally simple manner with high chemo- and site-selectivity, setting the stage for the challenging multiple site selective C–H functionalization. The mechanism is supported by a variety of experimental probes and theoretical investigations, including cyclic voltammetry tests, a bipolar ultramicroelectrode (BUME) methodology combined with nano-electrospray ionization mass spectrometry, and density functional theory calculations.

Graphical abstract: Electrochemical dual α,β-C(sp3)–H functionalization of cyclic N-aryl amines

Supplementary files

Article information

Article type
Paper
Submitted
31 jan 2023
Accepted
05 mar 2023
First published
09 mar 2023

Green Chem., 2023,25, 2681-2689

Electrochemical dual α,β-C(sp3)–H functionalization of cyclic N-aryl amines

T. Feng, Z. Zhu, D. Zhang, S. Wang, R. Li, Z. Zhu, X. Zhang and Y. Qiu, Green Chem., 2023, 25, 2681 DOI: 10.1039/D3GC00344B

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