Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C-N Bond Activation

被引：252
|
作者：
Maity, Prantik [1 ]
Shacklady-McAtee, Danielle M. [1 ]
Yap, Glenn P. A. [1 ]
Sirianni, Eric R. [1 ]
Watson, Mary P. [1 ]
机构：
[1] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 01期
基金：
美国国家科学基金会;
关键词：
ASYMMETRIC-SYNTHESIS; ARYLTRIMETHYLAMMONIUM IODIDES; ARYLBORONIC ACIDS; NEGISHI REACTIONS; CARBONATES; ALKYLATION; REAGENTS; PROTODEBORONATION; TRIARYLMETHANES; DIARYLMETHANES;
D O I：
10.1021/ja3089422
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines.
引用
收藏
页码：280 / 285
页数：6
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