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Regioselective benzannulation of allylic sulfur ylides with ynones: a rapid access to substituted thioanisoles

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Abstract

The efficiency and selectivity of annulation reactions are often difficult to control in the presence of multiple potential reactive centers, like in the case of allylic sulfur ylides (ASY). Here, we describe a novel base mediated [3+3] benzannulation of ASY and readily available alkynones, which accomplishes the regioselective formation of multisubstituted thioanisoles, highly sought after chemical scaffolds. A new reactivity pattern of ASY has been unearthed, where it acted as both a 3C component and sulfur source in benzannulation. Use of a widely available base, operational simplicity and broad substrate scope are the additional salient features of the conversion.

Graphical abstract: Regioselective benzannulation of allylic sulfur ylides with ynones: a rapid access to substituted thioanisoles

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Article information


Submitted
10 Aug 2020
Accepted
23 Sep 2020
First published
24 Sep 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Regioselective benzannulation of allylic sulfur ylides with ynones: a rapid access to substituted thioanisoles

M. Parameshwar, M. K. R. Singam, A. Nagireddy, J. B. Nanubolu and M. S. Reddy, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05436D

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