Ligandless microwave-assisted Pd/Cu-catalyzed direct arylation of oxazoles.
作者： François Besselièvre , Florence Mahuteau-Betzer , David S. Grierson , Sandrine Piguel
DOI: 10.1021/JO7027135
关键词: Catalysis 、 Copper 、 Oxazole 、 Aryl 、 Organic chemistry 、 Chemistry 、 Chemical synthesis 、 Palladium 、 Functional group 、 Ring (chemistry)
摘要: 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 the van Leusen oxazole ring synthesis, this methodology illustrated by an expedient two-step synthesis four 2,5-diaryloxazole alkaloids texamine, texaline, balsoxin, O-Me-halfordinol from commercially available starting materials.
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A.M. van Leusen, B.E. Hoogenboom, H. Siderius, A novel and efficient synthesis of oxazoles from tosylmethylisocyanide and carbonyl compounds Tetrahedron Letters. ,vol. 13, pp. 2369- 2372 ,(1972) , 10.1016/S0040-4039(01)85305-3
Masayuki Iwasaki, Hideki Yorimitsu, Koichiro Oshima, Microwave-assisted palladium-catalyzed direct arylation of 1,4-disubstituted 1,2,3-triazoles with aryl chlorides. Chemistry-an Asian Journal. ,vol. 2, pp. 1430- 1435 ,(2007) , 10.1002/ASIA.200700206
Esther Domínguez, Dolores Bad誕, Ester Lete, Mar誕-Jes徭 Villa, Luis Castedo, Domingo Dom地guez, On 5-Hydroxytetrahydroprotoberberine Derivatives. Synthetic Studies and Stereochemical Elucidation Heterocycles. ,vol. 27, pp. 687- 693 ,(1988) , 10.3987/COM-87-4375
Andrew S. Kende, Pawel Fludzinski, Chloroacetylenes as Michael acceptors. I. mechanism of enolate dichlorovinylation. Tetrahedron Letters. ,vol. 23, pp. 2369- 2372 ,(1982) , 10.1016/S0040-4039(00)87344-X
Anna C. Giddens, Helena I.M. Boshoff, Scott G. Franzblau, Clifton E. Barry, Brent R. Copp, Antimycobacterial natural products: synthesis and preliminary biological evaluation of the oxazole-containing alkaloid texaline Tetrahedron Letters. ,vol. 46, pp. 7355- 7357 ,(2005) , 10.1016/J.TETLET.2005.08.119
Alan P. Kozikowski, Anthony Ames, Oxazoles in organic chemistry. 2. Application to the synthesis of benzylisoquinoline alkaloids Journal of Organic Chemistry. ,vol. 45, pp. 2548- 2550 ,(1980) , 10.1021/JO01300A070
Hien-Quang Do, Olafs Daugulis, Copper-Catalyzed Arylation of Heterocycle C−H Bonds Journal of the American Chemical Society. ,vol. 129, pp. 12404- 12405 ,(2007) , 10.1021/JA075802+
Christophe Hoarau, Alexis Du Fou de Kerdaniel, Nicolas Bracq, Pierre Grandclaudon, Axel Couture, Francis Marsais, Regioselective palladium-catalyzed phenylation of ethyl 4-oxazolecarboxylate Tetrahedron Letters. ,vol. 46, pp. 8573- 8577 ,(2005) , 10.1016/J.TETLET.2005.09.192
Fabio Bellina, Chiara Calandri, Silvia Cauteruccio, Renzo Rossi, Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides Tetrahedron. ,vol. 63, pp. 1970- 1980 ,(2007) , 10.1016/J.TET.2006.12.068
Kevin J. Hodgetts, Mark T. Kershaw, Ethyl 2-Chlorooxazole-4-carboxylate: A Versatile Intermediate for the Synthesis of Substituted Oxazoles Organic Letters. ,vol. 4, pp. 2905- 2907 ,(2002) , 10.1021/OL0262800