ortho-Selective nucleophilic addition of amines to 3-borylbenzynes: synthesis of multisubstituted anilines by the triple role of the boryl group

Nucleophilic addition of amines to 3-[(dan)boryl]benzynes (dan = 1,8-diaminonaphthalene) generated by a fluoride ion proceeded with high ortho-selectivity to give 2-borylaniline derivatives, under conditions that are tolerant to various functional groups. The (dan)boryl group of the adduct was hydro...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2013-12, Vol.11 (46), p.8145-8150
Main Authors: Takagi, Akira, Ikawa, Takashi, Saito, Kozumo, Masuda, Shigeaki, Ito, Toyohiro, Akai, Shuji
Format: Article
Language:English
Subjects:
Amines - chemistry
Aniline Compounds - chemical synthesis
Aniline Compounds - chemistry
Benzene Derivatives - chemistry
Boron Compounds - chemistry
Models, Molecular
Molecular Structure
Quantum Theory
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Summary:Nucleophilic addition of amines to 3-[(dan)boryl]benzynes (dan = 1,8-diaminonaphthalene) generated by a fluoride ion proceeded with high ortho-selectivity to give 2-borylaniline derivatives, under conditions that are tolerant to various functional groups. The (dan)boryl group of the adduct was hydrolyzed into a boronic acid under acidic conditions, which could further serve for various C-C, C-O, C-N, and C-H bond-formation reactions. The overall process provides a promising entry for preparing multisubstituted aniline derivatives.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob41787e