Metal-Free One-Pot Conversion of Electron-Rich Aromatics into Aromatic Nitriles

Sousuke Ushijima, Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: togofaculty.chiba-u.jp

S. Ushijima, H. Togo, Synlett, 2010, 1067-1070.

DOI: 10.1055/s-0029-1219575

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Abstract

Various electron-rich aromatics could be smoothly converted into the corresponding aromatic nitriles in good yields by treatment with POCl₃ and DMF, followed by molecular iodine in aqueous ammonia. The present reaction is a novel metal-free one-pot method for the preparation of aromatic nitriles from electron-rich aromatics.

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Key Words

aromatics, aromatic N,N-dimethyliminium salts, aromatic nitriles, Vilsmeier-Haack reaction, molecular iodine, aqueous ammonia

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ID: J60-Y2010-1060