In situ generation and synthetic application of 2-phenylbenzimidazoline to the selective reduction of carbon-carbon double bonds of electron-deficient olefins.
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概要
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2-Phenylbenzimidazoline (PBI) as a mild, selective, and convenient reducing agent was efficiently generated in situ from <I>o</I>-phenylenediamine and benzaldehyde in alcohols. A generally applicable method for the selective reduction of carbon–carbon double bonds of a variety of electron-deficient olefins with an alcoholic solution of PBI is described. The reduction of α,β-unsaturated ketones to the corresponding saturated ketones could also be accomplished (but, less effectively) with PBI with the aid of a Lewis-acid catalyst. 1-Methyl-2-(<I>o</I>-nitrophenyl)benzimidazoline prepared and isolated by the reaction of <I>o</I>-nitrobenzaldehyde with <I>N</I>-methyl-<I>o</I>-phenylenediamine reduced benzylidenemalononitrile to give benzylmalononitrile and 1-methyl-2-(<I>o</I>-nitrophenyl)benzimidazole in high yields. This shows the validity of PBI to be the actual reducing species in the present reduction system. From a mechanistic study, the present reductions could be interpreted in terms of a mechanism involving a synchronous transport of a pair of hydrogens or a sequential transfer of a hydride and a proton from PBI to the olefins.
- 公益社団法人 日本化学会の論文
著者
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Chikashita Hidenori
Department Of Applied Chemistry Faculty Of Engineering Kansai University
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Itoh Kazuyoshi
Department Of Applied Chemistry Faculty Of Engineering & High Technology Research Center Kansai
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Miyazaki Makoto
Department Of Mechanical Engineering And Intelligent Systems The University Of Electro-communication
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Morita Yasuhiro
Department of Applied Chemistry, Faculty of Engineering, Kansai University
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Nishida Shuichi
Department of Applied Chemistry, Faculty of Engineering, Kansai University
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Miyazaki Makoto
Department of Applied Chemistry, Faculty of Engineering, Kansai University
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