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• W2069187716 abstract "Reaction of (Z)-styryl bromide (1) with PhB(OH)2 in toluene at 80 °C for 1 h in the presence of Pd(PPh3)4 (1.5 mol %) and an aqueous solution of K2CO3 (3 equiv) affords (Z)-stilbene as the cross-coupling product in 99% yield. On the other hand, the same reaction of the (E)-isomer of 1 forms considerable amounts of homocoupling products (1,4-diphenylbutadiene (2, 22%) and biphenyl (27%)) in addition to the cross-coupling product ((E)-stilbene, 73%). The formation of 2 was examined by kinetic experiments using trans-Pd(CH═CHPh)Br(PMePh2)2 (3) as a model of the presumed intermediate. Complex 3 reacts with 1 at 50 °C for 5 h, giving 2 (91%) and trans-PdBr2(PMePh2)2 (4, 92%), together with a small amount of Pd(η2-PhCH═CHPMePh2)Br(PMePh2) (5, 8%). The reaction rate shows first-order dependence on the concentration of 3 and 5, respectively, but is independent of the concentration of 1. A novel homocoupling process induced by P−C reductive elimination from 3 giving 5 is proposed." @default.
• W2069187716 created "2016-06-24" @default.
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• W2069187716 date "2008-02-01" @default.
• W2069187716 modified "2023-09-23" @default.
• W2069187716 title "Reaction of <i>trans</i>-Pd(styryl)Br(PMePh₂)₂ with Styryl Bromide Affording 1,4-Diphenylbutadiene. An Unexpected Homocoupling Process Induced by P−C Reductive Elimination" @default.
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• W2069187716 doi "https://doi.org/10.1021/om701128e" @default.
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