Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 50, Pages 14283-14287Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201100818
Keywords
amination; C-N coupling; heterogeneous catalysis; nanowires; platinum
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Funding
- National Natural Science Foundation of China [21003092]
- NSF of Jiangsu Province [BK2008158]
- New Faculty Start Foundation of Soochow University
- scientific innovation research of college graduate in Jiangsu province [CXZZ11_0102]
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Traditionally important in the pharmaceutical, agrochemical, and synthetic dye industries, C-N coupling has proved useful for the preparation of a number of valuable organic compounds. Here, a new method for the direct one-pot reductive C-N 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 C-N 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.
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