Palladium Cross-Couplings of Oxazoles
dc.contributor.advisor
Greaney, Michael F
en
dc.contributor.author
Flegeau, Emmanuel Ferrer
en
dc.date.accessioned
2009-11-03T15:56:48Z
dc.date.available
2009-11-03T15:56:48Z
dc.date.issued
2008
dc.description.abstract
A review covering the literature until April 2008 concerning organometallic
reactions to funcionalise oxazoles is described. A protocol for the functionalisation
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. In addition, a regioselective Suzuki-Miyaura cross-coupling of
2,4-dihalooxazoles followed by a Stille coupling has been successfully developed.
The procedure affords convergent syntheses of trisoxazoles in high yield and in a
minimum number of steps. Furthermore, C-2 direct arylation of oxazoles is
discussed. This methodology is extended to the synthesis of C2-C4’ linked bis and
tris oxazoles of the type found in the Ulapualide A family of natural products.
en
dc.identifier.uri
http://hdl.handle.net/1842/3171
dc.language.iso
en
dc.publisher
The University of Edinburgh
en
dc.subject
Chemistry
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dc.subject
Organic Chemistry
en
dc.title
Palladium Cross-Couplings of Oxazoles
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dc.type
Thesis or Dissertation
en
dc.type.qualificationlevel
Doctoral
en
dc.type.qualificationname
PhD Doctor of Philosophy
en
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