Mamoru Tobisu, H. Nakai, N. Chatani
Jun 18, 2009
Citations
0
Influential Citations
92
Citations
Quality indicators
Journal
The Journal of organic chemistry
Abstract
Air-stable and commercially available alkynophilic metal salts, such as PtCl2, PtCl4, and [RuCl2(CO)3]2, catalyze the cycloisomerization of 1-alkyl-2-ethynylbenzenes to produce substituted indenes even at an ambient temperature. Electrophilically activated alkynes can be intercepted by simple benzylic C-H bonds at primary, secondary, and tertiary carbon centers. Mechanistic studies, such as labeling studies and kinetic isotope and substituent effects, indicate that the cycloisomerization proceeds through the formation of a vinylidene intermediate and turnover-limiting 1,5-shift of benzylic hydrogen.