Preparation of (Z)-1-(3-nitrophenyl)-4-phenylbut-1-ene and (Z)-1-(3-nitrophenyl)-5-phenylpent-1-ene by Pd(0)-catalyzed cross-coupling reaction

Add time:08/16/2019    Source:sciencedirect.com

The two nitroolefins, (Z)-1-(3-nitrophenyl)-4-phenylbut-1-ene and (Z)-1-(3-nitrophenyl)-5-phenylpent-1-ene, were stereospecifically prepared by Pd(0)-catalyzed cross-coupling reaction between (Z)-β-bromo-3-nitrostyrene and 2-phenylethyl- or 3-phenylpropyl zinc chloride, respectively. The yield reached 60% in spite of the well-known tendency of aralkyl organometallic halides to undergo β-elimination during the catalytic reaction. Only Pd-complexes displayed a satisfactory catalytic activity, the presence of the nitro group destroying that of related Ni-derivatives.

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