Issue 10, 2024

A Mn(iii)-catalyzed arylboronic acid-based cascade reaction via a nonclassical organometallic-radical mechanism

Abstract

An efficient cascade reaction of arylboronic acids, o-cyanoaryl isocyanides, and indoles catalyzed by manganese(III) acetylacetonate which enables the construction of a series of 2-(1H-indol-3-yl)-2-phenylindolin-3-imines was developed. The transformation features high regioselectivity, broad substrate scope, and good functional group compatibility. Investigation of the reaction mechanism showed that instead of proceeding through a conventional radical pathway, the reaction possibly undergoes a nonclassical organometallic-radical route involving a sequence of transmetalation between arylboronic acid and Mn(acac)3, insertion of isocyanide, intramolecular nucleophilic cyclization, and nucleophilic addition of indole.

Graphical abstract: A Mn(iii)-catalyzed arylboronic acid-based cascade reaction via a nonclassical organometallic-radical mechanism

Supplementary files

Article information

Article type
Research Article
Submitted
05 Feb 2024
Accepted
21 Mar 2024
First published
22 Mar 2024

Org. Chem. Front., 2024,11, 2739-2746

A Mn(III)-catalyzed arylboronic acid-based cascade reaction via a nonclassical organometallic-radical mechanism

H. Qian, J. Zhang, S. Ji and X. Xu, Org. Chem. Front., 2024, 11, 2739 DOI: 10.1039/D4QO00244J

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