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In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and ( Z)-2-Alken-4-ynoates. | LitMetric
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In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and ( Z)-2-Alken-4-ynoates.

Linlin Xing Yong Zhang Bing Li Yunfei Du

Org Lett

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology , Tianjin University, Tianjin 300072 , China.

Published: May 2019

The reaction of diorganyl disulfides or diselenides with PhICl in acetonitrile was found for the first time to lead to the in situ formation of organosulfenyl chloride or selenenyl chloride, which enables the regioselective intramolecular chalcogenylacyloxylation of alkynes resulting in the formation of 4-chalcogenylisocumarins/pyrones in good to excellent yields under metal-free conditions.

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http://dx.doi.org/10.1021/acs.orglett.9b01046DOI Listing

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