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Synthesis 2006(8): 1325-1332
DOI: 10.1055/s-2006-926397
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
Further Information
Received
5 October 2005
Publication Date:
27 March 2006 (online)
Publication History
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.
Key words
hydroxyquinolines - cross-coupling - boron derivatives - halogenation - regioselectivity
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