One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols

被引：15

作者：

Ikawa, Takashi ^{[1
]}

Masuda, Shigeaki ^{[1
]}

Akai, Shuji ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Yamadaoka 1-6, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2020年 / 26卷 / 19期

基金：

日本学术振兴会;

关键词：

amination; amines; arynes; nucleophilic addition; synthetic methods; PALLADIUM-CATALYZED AMINATION; DIELS-ALDER REACTIONS; ARYL HALIDES; NUCLEOPHILIC-ADDITION; SELECTIVE SYNTHESIS; AMMONIA EQUIVALENT; PRIMARY AMINES; ARYNES; CHEMISTRY; MILD;

D O I：

10.1002/chem.201904987

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：4320 / 4332

页数：13

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