A Unified Strategy for Iron-Catalyzed ortho-Alkylation of Carboxamides

被引：132

作者：

Fruchey, Erin R. ^{[1
]}

Monks, Brendan M. ^{[1
]}

Cook, Silas P. ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 38期

关键词：

H BOND ACTIVATION; AROMATIC CARBOXAMIDES; ORTHO-ALLYLATION; DIRECT ARYLATION; METAL-COMPLEXES; ARYL PYRIDINES; HALIDES; IMINES; FUNCTIONALIZATIONS; DERIVATIVES;

D O I：

10.1021/ja506823u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Using 8-aminoquinoline-based aryl carboxamides, the direct ortho-alkylation can be achieved in high yields in the presence of an iron source, 1,2-bis(diphenyl-phosphino)ethane (dppe) and phenylmagnesium bromide. The reactions proceed without overalkylation and provide high levels of regioselectivity. The benzylation reactions can be performed in air with reagent-grade THF, while the alkylation works well with unactivated secondary bromides and iodides in 2-methyltetrahydrofuran. Moreover, the reactions only require 5-10 min.

引用

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页码：13130 / 13133

页数：4

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