期刊
ACS CATALYSIS
卷 8, 期 5, 页码 3943-3949出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b00116
关键词
nitroarenes; N-monomethylation; selective adsorption; paraformaldehyde; carbonyl group transformation
资金
- NSFC [21633013, 91745106]
- National Key Research and Development Program of China [2017YFA0403100]
- Key Research Program of Frontier Sciences of CAS [QYZDJ-SSW-SLH051]
The synthesis of N-monomethylamine remains a challenging topic because the N,N-dimethylation reaction is thermodynamically favorable. In this work, the kinetically controlled N-monomethylamine synthesis from nitroarene and paraformaldehyde/H-2 is reported to have superhigh N-monomethylamine selectivity in the presence of a Pd/TiO2 catalyst. The superior selectivity should be attributed to the preferential adsorption of the primary amine over Nmonomethylamine on the Pd/TiO2 surface, as elucidated by NH3/Me2NH-TPD, while the excellent catalytic activity could be associated with the good H-2 activation ability and high amine adsorbing capacity of the catalyst, as elucidated by NH3-TED and H-2-TPR tests. Good results were obtained with a variety of nitroarenes containing methyl, methoxyl, hydroxyl, fluoride, trifluoromethyl, ester, and amide substituents as starting materials, and the potential synthetic utility of this protocol in pharmaceutical is illustrated by N-monomethylation of drug molecules, such as clinidipine, nimesulide, procaine, and methyl aminosalicylate.
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