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Stereoselective synthesis of conjugated alkenynes via palladium-catalyzed coupling of alkenyl iodonium salts with terminal alkynes

✍ Scribed by N.Sh. Pirguliyev; V.K. Brel; N.S. Zefirov; P.J. Stang

Book ID
104209631
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
528 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

A novel method for stereospecific synthesis of conjugated alkenynes is suggested. The reaction of (E)-13-(trifluoromethanemlfonyloxy)-l-alkenyl iodonium trifluoromethanesulfonate with terminal alkynes in the presence of catalytic amounts of dichloro(triphenylphosphine)palladium(II) and CuI in aqueous medium proceeds stereospecifically to give the corresponding enynes in good yields. A possible mechanism for these cross-coupling reactions is discussed.

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