Azolium/Hydroquinone Organo-Radical Co-Catalysis: Aerobic C?C-Bond Cleavage in Ketones |
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Authors: | Yuya Nakatsuji Prof?Dr Yusuke Kobayashi Sakyo Masuda Prof?Dr Yoshiji Takemoto |
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Institution: | 1. Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Shimoadachi-cho, Yoshida, Sakyo-ku, Kyoto 606-8501 Japan;2. Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, 1 Misasagishichono-cho, Yamashina-ku, Kyoto, 607-8412 Japan |
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Abstract: | Organo-radical catalysts have recently attracted great interest, and the development of this field can be expected to broaden the applications of organocatalysis. Herein, the first example of a radical-generating system is reported that does not require any photoirradiation, radical initiators, or preactivated substrates. The oxidative C?C-bond cleavage of 2-substituted cyclohexanones was achieved using an azolium salt and a hydroquinone as co-catalysts. A catalytic mechanism was proposed based on the results of diffusion-ordered spectroscopy and cyclic voltammetry measurements, as well as computational studies. |
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Keywords: | azolium salt EDA complex organocatalysis radical catalysis |
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