酸催化苯胺与苯乙烯的邻位烷基化反应：一条合成带有庞大取代基的手性苯胺的改进路线。

Acid-catalyzed ortho-alkylation of anilines with styrenes: an improved route to chiral anilines with bulky substituents.

作者信息

Cherian Anna E, Domski Gregory J, Rose Jeffrey M, Lobkovsky Emil B, Coates Geoffrey W

机构信息

Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.

出版信息

Org Lett. 2005 Nov 10;7(23):5135-7. doi: 10.1021/ol051916j.

DOI:10.1021/ol051916j

PMID:16268521

Abstract

[reaction: see text] Reaction of para-substituted anilines with styrene derivatives at elevated temperatures, when catalyzed by CF3SO3H, results in highly chemoselective ortho-alkylation of the aniline. When R = H, dialkylation can be achieved by varying the ratio of styrene to aniline. Several different substituted anilines and styrenes were examined, and good yields (42-87%) were obtained, except in the case where electron-withdrawing substituents are present on the styrene.

摘要

[反应：见正文] 在高温下，对取代苯胺与苯乙烯衍生物在三氟甲磺酸（CF3SO3H）催化下反应，可实现苯胺的高化学选择性邻位烷基化。当R = H时，通过改变苯乙烯与苯胺的比例可实现二烷基化。研究了几种不同的取代苯胺和苯乙烯，除了苯乙烯上存在吸电子取代基的情况外，均获得了良好的产率（42 - 87%）。