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Communication | Special issue | Vol 86, No. 1, 2012, pp.171-180
Published online, 8th August, 2012
DOI: 10.3987/COM-12-S(N)70
Palladium-CATALYZED TANDEM COUPLING REACTION OF ALKYNE, CONJUGATED DIENE, AND TRIETHYLBORANE

Daiki Takushima, Masahiro Fukushima, Hideaki Satomura, Gen Onodera, and Masanari Kimura*

*Division of Chemistry and Materials Science, Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Pd(0) catalyst promotes three-component coupling reactions of allylic alcohols and vinylcyclopropanes with terminal alkynes and triethylborane to provide (E)-1-substituted 2-ethyl-1,4-pentadienes and (E)-1-substituted 2-ethyl-1,4-heptadienes involving geminal ethylation and allylation at the acetylenic terminal carbon atom with high regio- and stereoselectivities. 1,3-Butadiene and bis-dienes can act as allylating agents to undergo the multi-component coupling reactions, accompanied by dimerization of the diene moieties, to provide 1,4,9-decatrienes and pyrrolidines with excellent regio- and stereoselectivities.