Elsevier

Tetrahedron

Volume 55, Issue 27, 2 July 1999, Pages 8155-8167
Tetrahedron

Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis

https://doi.org/10.1016/S0040-4020(99)00297-5Get rights and content

Abstract

A novel 1,3-diene synthetic method from alkyne and ethylene was developed using ruthenium-catalyzed enyne metathesis. The reaction procedure is very simple: A CH2Cl2 solution of alkyne was stirred at room temperature under ethylene gas (1 atm.) in the presence of a catalytic amount of ruthenium benzylidene complex. The yield was good and the conversion yield was high. Dienes having functional groups such as a keto-carbonyl group, silyloxy group, ester, and ketal were synthesized from the corresponding alkynes and ethylene. In this reaction, the alkyne having a hetero atom at the propargylic position gave a good result and ether oxygen or amine nitrogen that coordinate strongly to the ruthenium catalyst prevents the reaction.

Novel 1,3-diene synthesis was developed from alkyne and ethylene in the presence of ruthenium carbene complex.

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