Ru-catalyzed ring-opening and substitution reactions of heteroaromatic compounds using propargylic carboxylates as precursors of vinylcarbenoids.

Org Lett

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

Published: April 2006

[reaction: see text] The reaction of heteroaromatic compounds with propargylic carboxylates in the presence of a catalytic amount of [RuCl(2)(CO)(3)](2) or PtCl(2) gives trienes in good yields. The key intermediate is an electrophilic (1-acetoxylvinyl)carbene complex generated from the activated propargylic acetates with transition metals.

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http://dx.doi.org/10.1021/ol0604769DOI Listing

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