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
收藏
页码:5529 / 5535
页数:7
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