Volume 38, Issue 13-14 pp. 2027-2029
Communication

Highly Selective Three-Component Coupling of Ethyl Propiolate, Alkenes, and Diphenyl Diselenide under Visible-Light Irradiation

Akiya Ogawa

Akiya Ogawa

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7414

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Mikio Doi

Mikio Doi

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7414

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Ikuko Ogawa

Ikuko Ogawa

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7414

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Toshikazu Hirao

Toshikazu Hirao

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7414

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Abstract

Just the right strength of carbon-radical trapping by diphenyl diselenide facilitates its selective three-component coupling with an electron-poor alkyne and an electron-rich alkene [Eq. (1)]. In contrast, (PhS)2 is too weak and (PhTe)2 too strong a radical trap, and polymerization of the unsaturated compounds and addition of (PhTe)2 to the alkyne occur, respectively.

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