Site-Selective C-H Annulation Reaction via Thianthrenium Salts of Arenes.

J Org Chem

State Key Laboratory of Anti-Infective Drug Discovery and Development; Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.

Published: July 2025


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Article Abstract

This work presents a site-selective C-H annulation strategy for dihydrobenzoisoxazole synthesis using readily accessible thianthrenium salts as aryne precursors. The process involves base-mediated generation of reactive aryne intermediates from thianthrenium salts followed by regioselective [3 + 2] cycloaddition with nitrone 1,3-dipoles, exhibiting excellent functional group tolerance and exceptional regiocontrol. The synthetic utility of this protocol is highlighted by the successful annulation of commercially available drug molecules, providing expedient access to novel scaffolds with potential bioactivity.

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http://dx.doi.org/10.1021/acs.joc.5c01106DOI Listing

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