Journal
CHEMSUSCHEM
Volume 13, Issue 1, Pages 116-120Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201902574
Keywords
amines; bismuth; imines; oxidation; photocatalysis
Funding
- National Natural Science Foundation of China [51872147, 21703109, 21671113]
- 111 Project of Hubei Province [2018-19-1]
- Program for Innovative Research Team of Science and Technology in the University of Henan Province [19IRTSTHN025]
- Funds of Young Teachers of Colleges of Henan Province [2017GGJS131]
- Natural Science Foundation of Nanyang Normal University [QN2017061, QN2016020]
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Photocatalytic selective oxidative coupling of amines is a promising method for imine synthesis. Bismuth-rich bismuth oxybromide photocatalysts have been found to exhibit improved conversion and selectivity for the visible-light-driven selective oxidative coupling of amines to imines in water. Benzylamines with either electron-withdrawing or electron-donating groups undergo good conversion (94-99 %) and excellent selectivity (93-98 %) to the corresponding imines. The average apparent quantum efficiency at 455 nm is 57.4 %. Active species trapping experiments, isotope experiments, and in situ infrared spectroscopy reveal that water both serves as solvent and participates in the coupling reaction as a reactant. This work provides a green and environmentally friendly method for the efficient synthesis of imines with bismuth-rich bismuth oxyhalides and reveals water is involved in the oxidative coupling mechanism of benzylamines.
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