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
J. Org. Chem., 2007, 72 (9), pp 3289–3292
DOI: 10.1021/jo062573l
Publication Date (Web): April 3, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rsliu@mx.nthu.edu.tw

Abstract

Abstract Image

Catalytic cyclization of 2-alkyl-1-ethynylbenzene derivatives was implemented by TpRuPPh3(CH3CN)2PF6 (10 mol %) in hot toluene (105 °C, 36−100 h) to form 1-substituted-1H-indene and 1-indanone products; such cyclizations proceeded more efficiently for substrates bearing electron-rich benzenes. We propose that the cyclization mechanism involves a 1,5-hydrogen shift of initial metal−vinylidene intermediate.

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History

  • Published In Issue April 27, 2007
  • Received December 15, 2006

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