Synthesis of conjugated (1E,3E)- and (1Z,3Z)-1,4-di(n-pyridyl) (or n-quinolyl)-1,3-butadienes from n-(2′-chloroethenyl)pyridine (or quinoline) |
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Authors: | JG Rodríguez Cristina Díaz-Oliva |
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Institution: | a Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma, Cantoblanco, 28049-Madrid, Spain b Departamento de Química Física Aplicada, Facultad de Ciencias, Universidad Autónoma, Cantoblanco, 28049-Madrid, Spain |
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Abstract: | 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. |
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Keywords: | Nickel complexes 1 4-Diaryl-1 3-butadienes Homocoupling Stereospecific hydrogenation |
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