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 des 2021
Accepted
01 feb 2022
First published
07 feb 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements