Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 694, Issue 4, Pages 486-493Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2008.09.058
Keywords
Gold(III); Iminophosphorane ligands; C-C coupling; 2,5-Disubstituted oxazoles
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Funding
- Spanish Ministry of Education and Science [CTQ2005-01037]
- Brooklyn College (CUNY)
- Diputacion General de Aragon (Aragon, Spain) [B021/2006]
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The reaction of K[AuCl4] with AgClO4 and iminophosphorane ligands (N, N-IM) Ph3P=NR [R = CH2-2-NC5H4 (1), C(O)-2-NC5H4 (2)] or Ph2PyP=NR [Py = -2-NC5H4; R = Ph (3), C(O) Ph (4)] (mol ratio 1:2.2:1) in acetonitrile affords complexes [AuCl2(N,N-IM)] ClO4 (5-8). These compounds are air- and moisture-stable and they have been evaluated in two types of catalytic processes. They have been found to be effective catalysts in the addition of 2-methylfuran or azulene to methyl vinyl ketone, as well as in the synthesis of 2,5-disubstituted oxazoles from N-propargylcarboxamides. The reactions proceed in mild conditions and with similar yields to those described for AuCl3. Using this method, oxazoles bearing a thiophene functional group 2-(2'-thienyl)-5-methylthiazole can be prepared in excellent yields. In all cases the intermediate 5-methylene-4,5-dihydroxazole can be observed by H-1 NMR. (C) 2008 Elsevier B.V. All rights reserved.
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