4.7 Article

Multicomponent Tandem Triple Functionalization of Indoles via a Directing-group-free Strategy

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 365, Issue 7, Pages 990-996

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202300208

Keywords

Multicomponent reactions; Indoles; Triple functionalization; Regioselectivity; Directing-group-free

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This study presents a directing-group-free, three-component tandem C3-acylation/C5,6-H disulfenylation method for the position-selective functionalization of the poorly reactive benzenoid nucleus of indoles. The protocol demonstrates exceptional regio- and chemo-selectivity, broad substrate scope, good functional group tolerance, and mild reaction conditions. Importantly, this method offers great potential for the development of general site-selective functionalization at the benzenoid nucleus of indoles without the requirement for neighboring activating groups.
The position-selective functionalization of the poorly reactive benzenoid nucleus of indoles has remained a great challenge in organic chemistry. Here we describe a directing-group-free, three-component tandem C3-acylation/C5,6-H disulfenylation of indoles via an iodine-, Lewis acid- and Bronsted acid-cooperated mediated strategy. This protocol is remarkable for its exceptional regio- and chemo-selectivity, broad substrate scope, good functional group tolerance and mild reaction conditions. Advantageously, the present protocol offers great potential for the development of general site-selective functionalization at the benzenoid nucleus of indoles, removing the requirement for neighbouring activating groups.

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