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Synthesis of 3-aminoBODIPY dyes via copper-catalyzed vicarious nucleophilic substitution of 2-halogeno derivatives

Lookup NU author(s): Dr Julian Knight, Rua Alnoman, Dr Paul Waddell

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Abstract

2-Halogeno BODIPYs undergo copper catalysed nucleophilic substitution with alkyl amines and anilines and an amide to give the corresponding 3-aminoBODIPY derivatives. The substrates are readily prepared by the regioselective 2-halogenation of the chemically robust, preformed BODIPYs thus providing an alternative to direct nucleophilic substitution of the corresponding 3-halogenoBODIPYs which requires regioselective 3-halogenation of the more sensitive dipyrromethane intermediate. 2-Halogenation expands the scope of vicarious substitution of BODIPYs to include weaker nitrogen nucleophiles.

Publication metadata

Author(s): Knight JG, Alnoman RB, Waddell PG

Publication type: Article

Publication status: Published

Journal: Organic and Biomolecular Chemistry

Year: 2015

Volume: 13

Issue: 12

Pages: 3819-3829

Print publication date: 12/03/2015

Online publication date: 17/02/2015

Acceptance date: 16/02/2015

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/C4OB02626H

DOI: 10.1039/C4OB02626H

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