Synthesis 2006(8): 1325-1332  
DOI: 10.1055/s-2006-926397
PAPER
© Georg Thieme Verlag Stuttgart · New York

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 Cardonea, Carla T. Cioffib, Gianluca M. Farinolab, Francesco Nasoa,b, Roberta Ragnib
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;
Further Information

Publication History

Received 5 October 2005
Publication Date:
27 March 2006 (online)

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.