Pd/C(en) Catalyzed Chemoselective Hydrogenation in the Presence of Aryl Nitriles
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概要
- 論文の詳細を見る
Aromatic nitriles are not only important components of natural products, pharmaceuticals, herbicides and agrochemicals but also a synthetic equivalent of various functionalities. The development of synthetic methods of aromatic nitriles have been increasing in terms of its usefulness. Since aromatic nitriles are susceptible to the hydrogenation, it has been desired for the development of chemoselective hydrogenation method with retention of nitrile groups. Pd/C is one of the most popular catalysts for hydrogenation and many of reducible functional groups such as multiple bonds, benzyl ethers, N-Cbzs, nitro groups and so on could be easily reduced under the conditions. Therefore, it is very difficult to achieve the chemoselective hydrogenation of substrates containing two or more reducible functional groups. We have found that a Pd/C catalyst formed an isolable complex with ethylenediamine (en) employed as catalytic poison, and the complex [Pd/C(en)] catalyzed chemoselective hydrogenation of a variety of reducible functionalities distinguishing O-benzyl, N-Cbz and O-TBDMS protective groups, benzyl alcohols and epoxides. In the course of these investigations, we found the aryl nitriles could survive under the Pd/C(en)-catalyzed hydrogenation conditions in THF whose choice is important for the effective suppression. This methodology could be applied to the selective hydrogenation of alkene and alkyne functionalities in the presence of aromatic nitrile.
- 公益社団法人日本薬学会の論文
- 2007-05-01
著者
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Fujita Yuki
Laboratory Of Medicinal Chemistry Gifu Pharmaceutical University
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SAJIKI Hironao
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University
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Maegawa Tomohiro
Laboratory Of Medicinal Chemistry Gifu Pharmaceutical University
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Maegawa Tomohiro
Laboratories Of Medicinal Chemistry Gifu Pharmaceutical University
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Sajiki Hironao
Laboratory Of Medicinal Chemistry Gifu Pharmaceutical University
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Sajiki Hironao
Laboratories Of Medicinal Chemistry Gifu Pharmaceutical University
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Sato Mutsumi
Reagent Research Laboratories Wako Pure Chemical Industries Ltd.
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SAKURAI Ai
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University
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AKASHI Akira
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University
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OONO Keiji
Reagent Research Laboratories, Wako Pure Chemical Industries, Ltd.
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Sakurai Ai
Laboratory Of Medicinal Chemistry Gifu Pharmaceutical University
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Oono Keiji
Reagent Research Laboratories Wako Pure Chemical Industries Ltd.
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Akashi Akira
Laboratory Of Medicinal Chemistry Gifu Pharmaceutical University
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Akashi Akira
Laboratory Of Chemistry And Technology Of Animal Products Faculty Of Agriculture Kyushu University
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Sajiki Hironao
Laboratories Of Medicinal Chemistry Gifu Pharmaceutical Univ.
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Maegawa Tomohiro
Laboratories Of Medicinal Chemistry Gifu Pharmaceutical Univ.
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