Ruthenium-Catalyzed Cyclization of 2-Alkyl-1-ethynylbenzenes via a 1,5-Hydrogen Shift of Ruthenium-Vinylidene Intermediates

Arjan Odedra, Swarup Datta and Rai-Shung Liu*

*Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, 30043, Republic of China, Email: rsliumx.nthu.edu.tw

A. Odedra, S. Datta, R.-S. Liu, J. Org. Chem., 2007, 72, 3289-3292.

DOI: 10.1021/jo062573l

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Abstract

Cyclization of electron-rich 2-alkyl-1-ethynylbenzene derivatives was catalyzed by TpRuPPh₃(CH₃CN)₂PF₆ in hot toluene to form 1-substituted-1H-indene and 1-indanone products. The cyclization mechanism involves a 1,5-hydrogen shift of an initial metal-vinylidene intermediate.

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Key Words

Cyclopentenones, Indenes, Indanones

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ID: J42-Y2007-1280