Cesium hydroxide promoted chemoselective N-alkylation for the generally efficient synthesis of secondary amines

RN Salvatore, AS Nagle, SE Schmidt, KW Jung

Index: Salvatore, Ralph N.; Nagle, Advait S.; Schmidt, Shaun E.; Jung, Kyung Woon Organic Letters, 1999 , vol. 1, # 12 p. 1893 - 1896

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Citation Number: 96

Abstract

Selective N-alkylation of primary amines was developed using cesium hydroxide to prepare various secondary amines efficiently. A cesium base not only promoted monoalkylations of primary amines but also suppressed overalkylations. Various amines and alkyl bromides were examined, and the preliminary results demonstrated this methodology was highly chemoselective, favoring mono-N-alkylation over dialkylation. In particular, use of amino ...