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Efficient synthesis of functionalized furans via ruthenium-catalyzed cyclization of epoxyalkyne derivatives
Journal article   Peer reviewed

Efficient synthesis of functionalized furans via ruthenium-catalyzed cyclization of epoxyalkyne derivatives

Ching-Yu Lo, Hongyun Guo, Jian-Jou Lian, Fwu-Ming Shen and Rai-Shung Liu
Journal of Organic Chemistry, Vol.67(11), pp.3930-3932
31/05/2002

Abstract

Ruthenium catalyst TpRuPPh 3 (CH 3 CN) 2 Cl is found to effect the cyclization of epoxyalkynes to furans in the presence of Et 3 N. The reactions worked well for various epoxyalkynes with suitable oxygen and nitrogen functionalities with low loading of catalyst. It failed with disubstituted epoxyalkynes. The mechanism was elucidated by a deuterium labeling experiment that suggested that the mechanism involved a ruthenium-vinylidenium intermediate.

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