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Direct Methylation of Amines with Carbon Dioxide and Molecular Hydrogen using Supported Gold Catalysts.

ChemSusChem (2015-09-15)
Xian-Long Du, Gao Tang, Hong-Liang Bao, Zheng Jiang, Xin-Hua Zhong, Dang Sheng Su, Jian-Qiang Wang
ABSTRACT

The N-methylation of amines with CO2 and H2 is an important step in the synthesis of bioactive compounds and chemical intermediates. The first heterogeneous Au catalyst is reported for this methylation reaction with good to excellent yields. The average turnover frequency (TOF) based on surface Au atoms is 45 h(-1) , which is the highest TOF value ever reported for the methylation of aniline with CO2 and H2 . Furthermore, the catalyst is tolerant toward a variety of amines, which includes aromatic, aliphatic, secondary, and primary amines. Preliminary mechanistic studies suggest that the N-alkyl formamide might be an intermediate in the N-methylation of amine process. Moreover, through a one-pot process, it is possible to convert primary amines, aldehydes, and CO2 into unsymmetrical tertiary amines with H2 as a reductant in the presence of the Au catalyst.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Octane, anhydrous, ≥99%
Sigma-Aldrich
Octane, reagent grade, 98%
Sigma-Aldrich
Octane, puriss. p.a., ≥99.0% (GC)
Sigma-Aldrich
Octane, electronic grade, ≥99.999% metals basis, ≥99% (CP)

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