Origin of regioselectivity in palladium-catalyzed cross-coupling reactions of polyhalogenated heterocycles

被引：255

作者：

Legault, Claude Y. ^{[1
]}

Garcia, Yeimy ^{[1
]}

Merlic, Craig A. ^{[1
]}

Houk, K. N. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 42期

关键词：

D O I：

10.1021/ja075785o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sequential cross-coupling on multihalogenated heterocycles is a particularly attractive strategy for the divergent synthesis of polysubstituted heterocycles, but the factors that govern the regioselectivity are not well understood. The present study shows that the selectivity in palladium-catalyzed cross-coupling reactions of heterocycles bearing multiple identical halogens is determined by both the energy to distort the carbon halogen bond to the transition-state geometry (related to BDE) and the interaction of the heterocycle pi* (LUMO) and PdL2 HOMO.

引用

页码：12664 / +

页数：3

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