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J Org Chem. 2017 Oct 20;82(20):11150-11156. doi: 10.1021/acs.joc.7b02175. Epub 2017 Oct 10.

Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Alkenyl Tosylates for the Synthesis of Enynones.

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1
Department of Chemistry, Chonnam National University , Gwangju 61186, Republic of Korea.

Abstract

A palladium-catalyzed decarboxylative coupling reaction was developed for the synthesis of 3-(1-alkynyl)-2-cyclohexen-1-ones. A variety of alkynyl carboxylic acids were coupled with 3-oxocyclohexenyl tosylates to afford the corresponding enynones in good to excellent yields. The developed catalytic system is phosphine free and showed good tolerance toward various functionalities such as chloride, cyano, nitro, ester, aldehyde, and alcohol groups. In addition, phenylpropiolic acid exhibited higher reactivity in the reaction with alkenyl toslyate than phenyl acetylene.

PMID:
28965408
DOI:
10.1021/acs.joc.7b02175

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