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Cs 2 CO 3 ‐Promoted Direct N ‐Alkylation: Highly Chemoselective Synthesis of N ‐Alkylated Benzylamines and Anilines
Author(s) -
Castillo JuanCarlos,
OrregoHernández Jessica,
Portilla Jaime
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600549
Subject(s) - chemistry , alkylation , anhydrous , halide , alkyl , organic chemistry , primary (astronomy) , catalysis , dimethylformamide , potassium carbonate , caesium , solubility , selectivity , physics , astronomy , solvent
Herein is described an efficient and chemoselective method for the synthesis of diversely substituted secondary amines in yields up to 98 %. Direct mono‐ N ‐alkylation of primary benzylamines and anilines with a wide range of alkyl halides is promoted by a cesium base in the absence of any additive or catalyst. The basicity and solubility of cesium carbonate in anhydrous N , N ‐dimethylformamide not only enables mono‐ N ‐alkylation of primary amines but also suppresses undesired dialkylation of the desired amines.