Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates
Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates
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DOI：
10.1021/ol050141b
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发表时间：
2005-03-17
期刊：
影响因子：
5.2
通讯作者：
Hartwig, JF
中科院分区：
文献类型：
--
作者：
Lee, DY;Hartwig, JF
我们报道Zn[N（SiMe3）（2）]（2）是一种温和的氨等价物和碱，用于芳基卤化物和三氟甲磺酸酯的钯催化胺化。与LiN（SiMe3）（2）相比，Zn[N（SiMe3）（2）]（2）和LiCl的组合与含有碱敏感官能团的芳基卤化物和三氟甲磺酸酯以高产率偶联。此外，芳基溴与芳基和烷基胺的偶联与Zn[N（SiMe 3）（2）]（2）和LiCl的组合作为碱。这些胺化反应发生时，光学活性酯的可烯醇化立构中心没有外消旋化。
[GRAPHICS]We report that Zn[N(SiMe3)(2)](2) is a mild ammonia equivalent and base for the palladium-catalyzed amination of aryl halides and triflates. In contrast to LiN(SiMe3)(2), the combination of Zn[N(SiMe3)(2)](2) and LiCl coupled with aryl halides and triflates containing base-sensitive functionality in high yields. In addition, aryl bromides coupled with aryl and alkylamines with the combination of Zn[N(SiMe3)(2)](2) and LiCl as base. These aminations occurred without racemization of the enolizable stereocenter of an optically active ester.