Cooperative Catalyst Effects in Palladium-Mediated Cyanation Reactions of Aryl Halides and Triflates
The Journal of Organic Chemistry1998Vol. 63(23), pp. 8224–8228
Citations Over TimeTop 10% of 1998 papers
Benjamin A. Anderson, Edward C. Bell, Francis O. Ginah, Nancy K. Harn, Lisa M. Pagh, James P. Wepsiec
Abstract
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.
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