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

Authors
Pirguliyev, NS Brel, VK Zefirov, NS Stang, PJ
Citation
Ns. Pirguliyev et al., Stereoselective synthesis of conjugated alkenynes via palladium-catalyzed coupling of alkenyl iodonium salts with terminal alkynes, TETRAHEDRON, 55(42), 1999, pp. 12377-12386
Citations number
47
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
42
Year of publication
1999
Pages
12377 - 12386
Database
ISI
SICI code
0040-4020(19991015)55:42<12377:SSOCAV>2.0.ZU;2-B
Abstract
A novel method for stereospecific synthesis of conjugated alkenynes is sugg ested. The reaction of (E)-[beta-(trifluoromethanesulfonyloxy)-1-alkenyl](p henyl) iodonium trifluoromethanesulfonate with terminal alkynes in the pres ence 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 react ions is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.