Selective Pd-Catalyzed Oxidative Coupling of Anilides with Olefins through C-H Bond Activation at Room Temperature

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• 作者：Maarten D. K. Boele ; Gino P. F. van Strijdonck ; Andr&eacute ; H. M. de Vries ; Paul C. J. Kamer ; Johannes G. de Vries ; and Piet W. N. M. van Leeuwen
• 刊名：Journal of the American Chemical Society
• 出版年：2002
• 出版时间：February 27, 2002
• 年：2002
• 卷：124
• 期：8
• 页码：1586 - 1587
• 全文大小：42K
• 年卷期：v.124,no.8(February 27, 2002)
• ISSN：1520-5126

文摘

Using a high-throughput experimentation approach we found a selective and mild Pd-catalyzed oxidative coupling reaction between anilide derivatives and acrylates that occurs through ortho C-H bond activation. The reaction is carried out in an acidic environment and occurs even at room temperature with use of a cheap oxidant (benzoquinone) in yields up to 91%. The benzoquinone possibly also functions as a ligand, stabilizing the catalyst. From the electronic dependence of the reaction and the observed kinetic isotope effect (k_H/k_D = 3) the key step of the catalytic cycle is believed to be electrophilic attack by a [PdOAc]⁺ complex on the chars/pi.gif" BORDER=0 >-system of the arene.