Issue 46, 2013

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
03 Aug 2013
Accepted
02 Oct 2013
First published
02 Oct 2013

Org. Biomol. Chem., 2013,11, 8145-8150

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

A. Takagi, T. Ikawa, K. Saito, S. Masuda, T. Ito and S. Akai, Org. Biomol. Chem., 2013, 11, 8145 DOI: 10.1039/C3OB41787E

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