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Molecules 2010, 15(6), 4189-4200; doi:10.3390/molecules15064189

Rhodium-Catalyzed Linear Codimerization and Cycloaddition of Ketenes with Alkynes

1
Advanced Biomedical Engineering Research Unit, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
2
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
3
Office of Society-Academia Collaboration for Innovation, Kyoto University, Yoshida-Honmachi, Sakyo-ku, Kyoto 606-8501, Japan
*
Author to whom correspondence should be addressed.
Received: 11 May 2010 / Revised: 25 May 2010 / Accepted: 7 June 2010 / Published: 9 June 2010
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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Abstract

A novel rhodium-catalyzed linear codimerization of alkyl phenyl ketenes with internal alkynes to dienones and a novel synthesis of furans by an unusual cycloaddition of diaryl ketenes with internal alkynes have been developed. These reactions proceed smoothly with the same rhodium catalyst, RhCl(PPh3)3, and are highly dependent on the structure and reactivity of the starting ketenes.
Keywords: rhodium; catalyst; ketene; alkyne; codimerization; cycloaddition rhodium; catalyst; ketene; alkyne; codimerization; cycloaddition
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Kondo, T.; Niimi, M.; Yoshida, Y.; Wada, K.; Mitsudo, T.-A.; Kimura, Y.; Toshimitsu, A. Rhodium-Catalyzed Linear Codimerization and Cycloaddition of Ketenes with Alkynes. Molecules 2010, 15, 4189-4200.

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