Neutral Flavins: Green and Robust Organocatalysts for Aerobic Hydrogenation of Olefins

Yasushi Imada*, Takahiro Kitagawa, Takashi Ohno, Hiroki Iida and Takeshi Naota*

*Department of Chemistry, Graduate School of Engineering Science, Osaka University, Machikaneyama, Toyonaka, Osaka 560-8531, Japan, Email: imadachem.es.osaka-u.ac.jp, naotachem.es.osaka-u.ac.jp

Y. Imada, T. Kitagawa, T. Ohno, H. Iida, T. Naota, Org. Lett., 2010, 12, 32-35.

DOI: 10.1021/ol902393p

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Abstract

Various olefins can be hydrogenated quantitatively with neutral, flavin-derived catalysts in the presence of hydrazine under an athomspheric pressure of O₂. A vitamin B₂ derivative acts as a highly efficient and robust catalyst for the environmentally benign process producing water and nitrogen gas as the only waste products.

see article for more examples

proposed catalytic cycle

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Flavin-Catalyzed Generation of Diimide: An Environmentally Friendly Method for the Aerobic Hydrogenation of Olefins

Y. Imada, H. Iida, T. Naota, J. Am. Chem. Soc., 2005, 127, 14544-14545.

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Key Words

hydrogenation, organocatalysis, flavins, hydrazine

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ID: J54-Y2010-0060