Synthesis of 2-hydroxy-3-substituted naphthoquinones using the Heck reaction

The first Heck coupling of a naphthoquinone nucleus in aqueous solution is described. The methodology is noteworthy for the use of ‘green’ chemistry and the ease of isolation of the products. An efficient Heck coupling of 2-hydroxy-3-iodo-naphthoquinone with a series of electron-deficient alkenes in...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2007-06, Vol.48 (23), p.3995-3998
Main Authors: Perez, Alice L., Lamoureux, G., Zhen-Wu, Bi Yun
Format: Article
Language:English
Subjects:
2-Hydroxy-3-iodonaphthoquinone
Heck reaction
Hooker condensation
Naphthoquinone
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The first Heck coupling of a naphthoquinone nucleus in aqueous solution is described. The methodology is noteworthy for the use of ‘green’ chemistry and the ease of isolation of the products. An efficient Heck coupling of 2-hydroxy-3-iodo-naphthoquinone with a series of electron-deficient alkenes in aqueous solution has been accomplished. The method is characterized by simple conditions and facile work-up to isolate the products in good to excellent yields. The products contain the motif present in several naphthoquinone pigments but with enhanced polarity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.04.033