Issue 4, 2022

Electrochemical-induced benzyl C–H amination towards the synthesis of isoindolinones via aroyloxy radical-mediated C–H activation

Abstract

The rapid synthesis of valuable isoindolinones with cheap and easily available starting materials under mild conditions is of great importance, but is challenging. We enclose here a novel electrochemical strategy to selectively and sustainably access isoindolinone using simple o-alkyl benzoic acids and nitriles as substrates under metal catalyst and external oxidant-free conditions. The protocol shows a very good functional group tolerance. Mechanistic investigations suggest that aroyloxy radicals are involved in this transformation, which initiates the benzylic C–H amination event by a 1,5-HAT process. Meanwhile, nitrile as the nitrogen source plays a vital role, as its derived intermediate facilitates the construction of the amide bond in the product.

Graphical abstract: Electrochemical-induced benzyl C–H amination towards the synthesis of isoindolinones via aroyloxy radical-mediated C–H activation

Supplementary files

Article information

Article type
Communication
Submitted
15 dez 2021
Accepted
01 fev 2022
First published
07 fev 2022

Green Chem., 2022,24, 1445-1450

Electrochemical-induced benzyl C–H amination towards the synthesis of isoindolinones via aroyloxy radical-mediated C–H activation

M. Yu, Y. Gao, L. Zhang, Y. Zhang, Y. Zhang, H. Yi, Z. Huang and A. Lei, Green Chem., 2022, 24, 1445 DOI: 10.1039/D1GC04676D

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