三甲基硅烷基锌酰胺作为一种温和的氨等价物及用于芳基卤化物和三氟甲磺酸酯胺化反应的碱。

Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates.

作者信息

Lee Dae-Yon, Hartwig John F

机构信息

Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 6520-8107, USA.

出版信息

Org Lett. 2005 Mar 17;7(6):1169-72. doi: 10.1021/ol050141b.

DOI:10.1021/ol050141b

PMID:15760166

Abstract

[reaction: see text] We report that ZnN(SiMe(3))(2) is a mild ammonia equivalent and base for the palladium-catalyzed amination of aryl halides and triflates. In contrast to LiN(SiMe(3))(2), the combination of ZnN(SiMe(3))(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 ZnN(SiMe(3))(2) and LiCl as base. These aminations occurred without racemization of the enolizable stereocenter of an optically active ester.

摘要

[反应：见正文] 我们报道了ZnN(SiMe(3))(2)是一种温和的氨替代物及碱，可用于钯催化的芳基卤化物和三氟甲磺酸酯的胺化反应。与LiN(SiMe(3))(2)不同，ZnN(SiMe(3))(2)与LiCl的组合能使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反应。此外，芳基溴化物与芳基胺和烷基胺在ZnN(SiMe(3))(2)和LiCl组合作为碱的条件下发生反应。这些胺化反应不会使光学活性酯的可烯醇化立体中心发生外消旋化。