Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides

被引：296

作者：

Hooper, MW ^{[1
]}

Utsunomiya, M ^{[1
]}

Hartwig, JF ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 07期

关键词：

D O I：

10.1021/jo0266339

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Detailed studies have been conducted to determine the activity of palladium catalysts for the amination of five-membered heterocyclic halides and to determine the factors that control the scope of this reaction. Palladium-catalyzed aminations of the electron-rich furanyl, thiophenyl, and indolyl halides and of the related 2-halogenated thiazoles, benzimidazole, and benzoxazole have been shown to occur with a subset of amines. Various combinations of palladium precursors and (PBu3)-Bu-t were tested as catalysts for reaction of 3-bromothiophene with N-methylaniline, and the fastest reactions occurred with the Pd(I) dimer, [PdBr((PBu3)-Bu-t)](2). The fastest aminations of thiazoles, benzimidazoles, and benzoxazoles occurred with the combination of palladium trifluoroacetate and (PBu3)-Bu-t as catalyst.

引用

页码：2861 / 2873

页数：13

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