A Mn(iii)-catalyzed arylboronic acid-based cascade reaction via a nonclassical organometallic-radical mechanism†
Shun-Jun
Ji 
*a
and
Xiao-Ping
Xu
*ab
*a
and
Xiao-Ping
Xu
*ab
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.
- This article is part of the themed collection: 2024 Organic Chemistry Frontiers HOT articles
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