Ligandless Microwave-Assisted Pd/Cu-Catalyzed Direct Arylation of Oxazoles

An efficient microwave-assisted palladium/copper co-mediated direct arylation of oxazoles with aryl bromides under ligandless conditions has been developed. The method is functional group tolerant and provides rapid access to medicinally relevant compounds in good yields. Coupled to the van Leusen o...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-04, Vol.73 (8), p.3278-3280
Main Authors: Besselièvre, François, Mahuteau-Betzer, Florence, Grierson, David S., Piguel, Sandrine
Format: Article
Language:English
Subjects:
Bromides - chemistry
Catalysis
Chemical Sciences
Chemistry
Copper - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Ligands
Microwaves
Molecular Structure
Organic chemistry
Oxazoles - chemistry
Palladium - chemistry
Preparations and properties
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Summary:An efficient microwave-assisted palladium/copper co-mediated direct arylation of oxazoles with aryl bromides under ligandless conditions has been developed. The method is functional group tolerant and provides rapid access to medicinally relevant compounds in good yields. Coupled to the van Leusen oxazole ring synthesis, this methodology is illustrated by an expedient two-step synthesis of the four 2,5-diaryloxazole alkaloids texamine, texaline, balsoxin, and O-Me-halfordinol from commercially available starting materials.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo7027135