Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates

Overview

Journal JACS Au

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Apr 1

PMID 38559716

Authors

Daksh Singh Davas

Dinesh Kumar Gopalakrishnan

Sandeep Kumar

Anmol

Tarak Karmakar

Janakiram Vaitla

Affiliations

Soon will be listed here.

Abstract

Herein, we report a highly regioselective [4 + 2]-annulation of vinyl sulfoxonium ylides with ynoates under light-mediated conditions. The reaction proceeds through the new dienyl sulfoxonium ylide, which undergoes photolysis under blue light irradiation to give highly substituted naphthalene scaffolds. The method presented here operates at room temperature and does not require the addition of an external photosensitizer. The generated dienyl sulfoxonium ylide absorbs light and acts as a photosensitizer for the formation of arenes. The synthetic potential of these benzannulations was further illustrated by various synthetic transformations and a scale-up reaction. Moreover, control experiments and quantum chemical calculations reveal the mechanistic details of the developed reaction.

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