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Ultrathin Platinum Nanowire Catalysts for Direct CN Coupling of Carbonyls with Aromatic Nitro Compounds under 1 Bar of Hydrogen
Author(s) -
Hu Lei,
Cao Xueqin,
Ge Danhua,
Hong Haiyan,
Guo Zhiqiang,
Chen Liang,
Sun Xuhui,
Tang Jianxin,
Zheng Junwei,
Lu Jianmei,
Gu Hongwei
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100818
Subject(s) - chemistry , catalysis , platinum , amination , intramolecular force , reductive amination , nitro , imine , hydrogen , coupling reaction , intermolecular force , hydrogen storage , hydrazine (antidepressant) , photochemistry , combinatorial chemistry , organic chemistry , molecule , alkyl , chromatography
Traditionally important in the pharmaceutical, agrochemical, and synthetic dye industries, CN coupling has proved useful for the preparation of a number of valuable organic compounds. Here, a new method for the direct one‐pot reductive CN coupling from carbonyl and aromatic nitro compounds is described. Employing ultrathin platinum nanowires as the catalyst and hydrogen as the reducing agent, N ‐alkylamines were achieved in high yields. Debenzylation products were not detected after prolonged reaction times. Time‐dependent analysis, ReactIR spectroscopy and DFT calculations revealed that the CN coupling proceeded through a different mechanism than traditional “reductive amination.” N ‐Alkylamines were directly obtained by intermolecular dehydration over platinum nanowires under a hydrogen atmosphere, instead of intramolecular water elimination and imine hydrogenation.