Org. Lett., 8 (12), 2495 -2498, 2006. 10.1021/ol060591j S1523-7060(06)00591-8
Web Release Date: May 11, 2006

Copyright © 2006 American Chemical Society

Suzuki Coupling of Oxazoles

Emmanuel Ferrer Flegeau, Matthew E. Popkin, and Michael F. Greaney*

University of Edinburgh, School of Chemistry, Joseph Black Building, King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, U.K., and GlaxoSmithKline, Chemical Development, Old Powder Mills, Tonbridge, Kent, TN11 9AN, U.K.

Michael.Greaney@ed.ac.uk

Received March 10, 2006

Abstract:

A protocol for the functionalization of the oxazole 2- and 4-positions using the Suzuki coupling reaction is described. 2-Aryl-4-trifloyloxazoles undergo rapid, microwave-assisted coupling with a range of aryl and heteroaryl boronic acids in good to excellent yields. The methodology is similarly effective using 4-aryl-2-chlorooxazoles as the coupling partner and has been extended to the synthesis of a novel class of homo- and heterodimeric 4,4-linked dioxazoles.


Download the full text: PDF | HTML