Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 19, Pages 4320-4332Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201904987
Keywords
amination; amines; arynes; nucleophilic addition; synthetic methods
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Funding
- Grants-in-Aid for Scientific Research [16K08164, 15J06024] Funding Source: KAKEN
- Japan Agency for Medical Research and Development [JP19am0101084] Funding Source: Medline
- Japan Society for the Promotion of Science [16K08164, 15J06024] Funding Source: Medline
- Kobayashi International Scholarship Foundation Funding Source: Medline
- Research Foundation for Pharmaceutical Sciences Funding Source: Medline
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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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