Ikawa, T; Masuda, S; Akai, S in [Ikawa, Takashi; Masuda, Shigeaki; Akai, Shuji] Osaka Univ, Grad Sch Pharmaceut Sci, Yamadaoka 1-6, Suita, Osaka 5650871, Japan published One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols in 2020, Cited 112. Recommanded Product: 150-19-6. The Name is m-Methoxyphenol. Through research, I have a further understanding and discovery of 150-19-6.
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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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles