Aryl to aryl palladium migration in the Heck and Suzuki coupling of o-halobiaryls

被引：100

作者：

Campo, Marino A. ^{[1
]}

Zhang, Haiming ^{[1
]}

Yao, Tuanli ^{[1
]}

Ibdah, Abdellatif ^{[1
]}

McCulla, Ryan D. ^{[1
]}

Huang, Qinhua ^{[1
]}

Zhao, Jian ^{[1
]}

Jenks, William S. ^{[1
]}

Larock, Richard C. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 19期

关键词：

D O I：

10.1021/ja069238z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel 1,4-palladium migration between the o- and o'-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this migration have been trapped either by a Heck reaction employing ethyl acrylate or by Suzuki cross-coupling using arylboronic acids. This palladium migration can be activated or deactivated by choosing the appropriate reaction conditions. Chemical and computational evidence supports the presence of an equilibrium that correlates with the C-H acidity of the available arene positions.

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页码：6298 / 6307

页数：10

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