Cesium effect: High chemoselectivity in direct N-alkylation of amines

RN Salvatore, AS Nagle, KW Jung

Index: Salvatore, Ralph Nicholas; Nagle, Advait S.; Kyung, Woon Jung Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 674 - 683

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Citation Number: 202

Abstract

A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to ...