A Straightforward Methodology for the Introduction of Aryl and Vinyl Substituents­ in the 5 or 7 Position of 8-Hydroxyquinoline

Francesco Babudri; Antonio Cardone; Carla T. Cioffi; Gianluca M. Farinola; Francesco Naso; Roberta Ragni

doi:10.1055/s-2006-926397

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A Straightforward Methodology for the Introduction of Aryl and Vinyl Substituents in the 5 or 7 Position of 8-Hydroxyquinoline

Francesco Babudri*^a,b, Antonio Cardone^a, Carla T. Cioffi^b, Gianluca M. Farinola^b, Francesco Naso^a,b, Roberta Ragni^b
^a CNR Istituto di Chimica dei Composti OrganoMetallici, via Orabona 4, 70126 Bari, Italy
^b Dipartimento di Chimica, Università degli Studi di Bari, via Orabona 4, 70126 Bari, Italy
Fax: +39(080)5442924; e-Mail: babudri@chimica.uniba.it;

Abstract

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Abstract

A straightforward and general procedure for the introduction of aryl and vinyl substituents in the 5 or 7 position of 8-hydroxyquinoline has been developed. The methodology presented is based upon the Suzuki cross-coupling reaction of aryl or vinyl halides with 5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)quinolin-8-ol or 7-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)quinolin-8-ol, respectively, that have been obtained regioselectively starting from 8-hydroxyquinoline.

Key words

hydroxyquinolines - cross-coupling - boron derivatives - halogenation - regioselectivity

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A Straightforward Methodology for the Introduction of Aryl and Vinyl Substituents­ in the 5 or 7 Position of 8-Hydroxyquinoline

A Straightforward Methodology for the Introduction of Aryl and Vinyl Substituents in the 5 or 7 Position of 8-Hydroxyquinoline