☆ 4.7 Article

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

JOURNAL OF ORGANIC CHEMISTRY (2017)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 82, 期 20, 页码 11150-11156

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AMER CHEMICAL SOC

DOI: 10.1021/acs.joc.7b02175

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Chemistry, Organic

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National Research Foundation of Korea (NRF) - Korea government (MSIP) [NRF-2012M3A7B4049655, NRF-2015R1A4A1041036]
National Research Foundation of Korea [2012M3A7B4049655] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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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.

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