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Journal Article

Bi(I)-Catalyzed Transfer-Hydrogenation with Ammonia-Borane

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Wang,  Feng
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Planas,  Oriol
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons207433

Cornella,  Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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ja9b00594_si_001.pdf
(Supplementary material), 6MB

Citation

Wang, F., Planas, O., & Cornella, J. (2019). Bi(I)-Catalyzed Transfer-Hydrogenation with Ammonia-Borane. Journal of the American Chemical Society, 141(10), 4235-4240. doi:10.1021/jacs.9b00594.


Cite as: http://hdl.handle.net/21.11116/0000-0003-397A-5
Abstract
A catalytic transfer-hydrogenation utilizing a well-defined Bi(I) complex as catalyst and ammonia-borane as transfer agent has been developed. This transformation represents a unique example of low-valent pnictogen catalysis cycling between oxidation states I and III, and proved useful for the hydrogenation of azoarenes and the partial reduction of nitroarenes. Interestingly, the bismuthinidene catalyst performs well in the presence of low-valent transition-metal sensitive functional groups and presents orthogonal reactivity compared to analogous phosphorus-based catalysis. Mechanistic investigations suggest the intermediacy of an elusive bismuthine species, which is proposed to be responsible for the hydrogenation and the formation of hydrogen.