The Journal of organic chemistry

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

A Odedra, S Datta, RS Liu

Index: Odedra, Arjan; Datta, Swarup; Liu, Rai-Shung Journal of Organic Chemistry, 2007 , vol. 72, # 9 p. 3289 - 3292

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Citation Number: 57

Abstract

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- 1 H-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.