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Article Abstract
A highly regioselective gold-catalyzed single oxygen transfer reaction, involving internal trifluoromethylated alkynes, pyridine -oxides, and nitriles, has been developed. The alkyne-attached CF-moiety functions through an inductive mechanism to direct -nucleophilic attack specifically to the β-alkyne position. This three-component transformation yields a diverse array of valuable 4-trifluoromethylated oxazoles in high yields (30 examples; up to 96%) under relatively mild gold-catalyzed conditions, demonstrating significant tolerance for various functional groups. The mechanistic experiments indicate the crucial role of the alkyne-attached CF-group for the formation of the oxazole products. The potential for the facile modification of the directing CF-group was also demonstrated.
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| http://dx.doi.org/10.1021/acs.joc.5c01570 | DOI Listing |
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