Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls

Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls

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 cr...

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Veröffentlicht in:Journal of the American Chemical Society 2007-05, Vol.129 (19), p.6298-6307
Hauptverfasser: Campo, Marino A, Zhang, Haiming, Yao, Tuanli, Ibdah, Abdellatif, McCulla, Ryan D, Huang, Qinhua, Zhao, Jian, Jenks, William S, Larock, Richard C
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container_end_page 6307
container_issue 19
container_start_page 6298
container_title Journal of the American Chemical Society
container_volume 129
creator Campo, Marino A
Zhang, Haiming
Yao, Tuanli
Ibdah, Abdellatif
McCulla, Ryan D
Huang, Qinhua
Zhao, Jian
Jenks, William S
Larock, Richard C
description 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.
doi_str_mv 10.1021/ja069238z
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title Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls
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