Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates

被引：157

作者：

Anderson, BA ^{[1
]}

Bell, EC ^{[1
]}

Ginah, FO ^{[1
]}

Harn, NK ^{[1
]}

Pagh, LM ^{[1
]}

Wepsiec, JP ^{[1
]}

机构：

[1] Lilly Res Labs, Chem Proc Res & Dev Div, Indianapolis, IN 46285 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 23期

关键词：

D O I：

10.1021/jo9808674

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substoichiometric quantities of copper or zinc species dramatically improve both conversion rate and efficiency of Pd(0)-catalyzed cyanation reactions. The optimum reaction conditions involve the use of a nitrile solvent, NaCN, and a catalyst system employing the combination of cuprous iodide with tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)(4)]. Beneficial effects were observed for the conversion of aryl halides, aryl triflates, and a vinyl bromide to the corresponding nitriles. The process was demonstrated on preparative scale with a broad range of aromatic and heteroaromatic substrates containing diverse functionality. A dual catalytic cycle is proposed to explain the profound influences of the cocatalyst system.

引用

页码：8224 / 8228

页数：5

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