期刊
JOURNAL OF ORGANOMETALLIC CHEMISTRY
卷 696, 期 1, 页码 331-337出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2010.09.059
关键词
2-Aryloxazoles; Aryl amides; Cyclizations; Homogenous catalysis; Propargylic alcohols; Ytterbium
资金
- University Research Committee, Nanyang Technological University [RG55/06]
- Science and Engineering Research Council, A*STAR, Singapore [092 1010 053]
- Yousef Jameel Scholarship
An efficient synthetic method to prepare di- and trisubstituted 2-aryloxazoles based on Yb(OTf)(3) catalyzed cyclization of trisubstituted propargylic alcohols with aryl amides is described. The reaction was accomplished in moderate to excellent product yields and with complete regioselective control. The mechanism is suggested to involve activation of the starting alcohol by the metal catalyst that results in its ionization. Subsequent cyclization of this newly generated carbocationic species with the aryl amide then affords the oxazole. In view of the mild conditions along with the low cost, commercially availability of Yb( OTf) 3 and its high tolerance to air and moisture, the present synthetic approach offers an operationally simplistic and convenient route to this important aromatic heterocycle. (C) 2010 Elsevier B.V. All rights reserved.
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