Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides
Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides
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DOI：
10.1021/jo0266339
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发表时间：
2003-04-04
影响因子：
3.6
通讯作者：
Hartwig, JF
中科院分区：
文献类型：
--
作者：
Hooper, MW;Utsunomiya, M;Hartwig, JF
已经进行了详细的研究，以确定钯催化剂的五元杂环卤化物的胺化的活性，并确定控制该反应的范围的因素。富电子的呋喃基、噻吩基和吲哚基卤化物以及相关的2-卤代噻唑、苯并咪唑和苯并恶唑的钯催化胺化反应已被证明与胺的子集一起发生。测试了钯前体和（PBu 3）-Bu-t的各种组合作为3-溴噻吩与N-甲基苯胺反应的催化剂，并且最快的反应发生在Pd（I）二聚体[PdBr（（PBu 3）-Bu-t）]（2）。噻唑、苯并咪唑和苯并恶唑的最快胺化反应发生在三氟乙酸钯和（PBu 3）-Bu-t作为催化剂的组合下。
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.