Journal
TETRAHEDRON
Volume 65, Issue 12, Pages 2512-2517Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.01.050
Keywords
Nickel complexes; 1,4-Diaryl-1,3-butadienes; Homocoupling; Stereospecific hydrogenation
Categories
Funding
- CAM
- MEC [S-0505/PPQ/0344, CFQ-2006-15692-C02-01]
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The homocoupling reaction between the conjugated n-(2-chloroethenyl)pyridine; n, 2-, 3- and 4- (or quinoline; n, 2- and 4-) mediated by zero-valent nickel complexes at room temperature affords to the corresponding 1,4-diaryl-1,3-butadiene, always as the 1E,3E stereoisomer. The yield in 1,4-diaryl-1,3-butadiene increases with the nickel catalyst and hence, the active zero-valent nickel catalyst is not regenerated during the homocoupling reaction. The stereospecific synthesis of (1Z,3Z)-1,4-di(4'-pyridyl)-1,3-butadiene stereoisomer was efficiently carried Out by partial hydrogenation of the appropriate 1,4-di(4'-pyridyl)-1,3-butadiyne. (C) 2009 Elsevier Ltd. All rights reserved.
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