52986-64-8Relevant academic research and scientific papers
Synthesis of unsymmetric tertiary amines via alcohol amination
Pang, Shaofeng,Deng, Youquan,Shi, Feng
supporting information, p. 9471 - 9474 (2015/06/08)
The first one-pot selective synthesis of unsymmetric tertiary amines is reported by the amination of two types of alcohols with primary amines via the development of a simple CuAlOx-HT catalyst and enables the synthesis of unsymmetric amines in a wide variety of primary amines and alcohols.
Selective N,N-dibenzylation of primary aliphatic amines with dibenzyl carbonate in the presence of phosphonium salts
Loris, Alessandro,Perosa, Alvise,Selva, Maurizio,Tundo, Pietro
, p. 3953 - 3956 (2007/10/03)
In the presence of catalytic amounts of tetraalkylphosphonium salts and under solventless conditions, primary aliphatic amines (RNH2: R = PhCH2, Ph(CH2)2, n-decyl, and 1-naphthylmethyl) are efficiently N-benzylated to the corresponding RN(CH2Ph) 2, using dibenzyl carbonate as the benzylating reagent. Compared to the reaction run without salt, where the competitive formation of the benzyl carbamate is favored, the phosphonium salt promotes high selectivity toward the benzylated amine and an increase of the reaction rate as well. However, in a single case explored for an amino acidic compound, namely 4-(aminomethyl) benzoic acid [4-(NH2CH2)C6H4CO 2H], both N,N-dibenzylation and esterification of the acid group were observed. Analysis of the IR vibrational modes of benzylamine in the presence of tetrabutylphosphonium bromide supports the hypothesis that this enhanced selectivity may be due to an acid-base interaction between the salt and the amine, which increases the steric bulk of the amine and favors attack of the nucleophile on the less hindered alkyl terminus of dibenzyl carbonate.
