Direct palladium-catalyzed C-3 arylation of free (NH)-indoles with aryl bromides under ligandless conditions

被引：154

作者：

Bellina, Fabio ^{[1
]}

Benelli, Francesca ^{[1
]}

Rossi, Renzo ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56125 Pisa, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 14期

关键词：

D O I：

10.1021/jo8007572

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the efficient, practical, and highly regioselective direct palladium-catalyzed C-3 arylation of free (NH)-indole and its electron-rich 1-unsubstituted derivatives under ligandless conditions is described. The reactions, which are run outside a glovebox without purification of solvent and reagents, involve treatment of free (NH)-indoles with activated, unactivated, and deactivated aryl bromides in refluxing toluene in the presence of K2CO3 as the base and a catalyst system consisting of a combination of Pd(OAc)(2) and benzyl(tributyl)ammonium chloride. The experimental results are consistent with a catalytic cycle based on an electrophilic palladation pathway at the 3-position of 1-indolyl potassium salts.

引用

页码：5529 / 5535

页数：7

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