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Ruthenium-catalyzed cyclization of 2-alkyl-1-ethynylbenzenes via a 1,5-hydrogen shift of ruthenium-vinylidene intermediates
Journal article   Peer reviewed

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
Journal of Organic Chemistry, Vol.72(9), pp.3289-3292
27/04/2007

Abstract

(Chemical Equation Presented) Catalytic cyclization of 2-alkyl-1- ethynylbenzene derivatives was implemented by TpRuPPh 3 (CH 3 CN) 2 PF 6 (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. © 2007 American Chemical Society.

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