Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation

被引：189
|
作者：
Duefert, M. Alexander [1 ]
Billingsley, Kelvin L. [1 ]
Buchwald, Stephen L. [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 34期
基金：
美国国家卫生研究院;
关键词：
OXIDATIVE ADDITION; PALLADIUM; COMPLEXES; ARYL; REACTIVITY; EFFICIENT; LIGAND; FUNCTIONALIZATION; CATALYST; HALIDES;
D O I：
10.1021/ja4064469
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. The procedure allows for the reaction of variously substituted indazole, benzimidazole, pyrazole, indole, oxindole, and azaindole halides under mild conditions in good to excellent yields. Additionally, the mechanism behind the inhibitory effect of unprotected azoles on Pd-catalyzed cross-coupling reactions is described based on evidence gained through experimental, crystallographic, and theoretical investigations.
引用
收藏
页码：12877 / 12885
页数：9
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