One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols |
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Authors: | Dr Takashi Ikawa Dr Shigeaki Masuda Prof Shuji Akai |
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Institution: | Graduate School of Pharmaceutical Sciences, Osaka University, Yamadaoka 1–6, Suita, Osaka, 565-0871 Japan |
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Abstract: | Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines. |
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Keywords: | amination amines arynes nucleophilic addition synthetic methods |
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