4.5 Article

Visible-Light Induced Oxidative Annulation of Enamides to 2,4,5-Trisubstituted Oxazole Skeletons

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 12, Issue 5, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202300019

Keywords

Enamides; Hydrogen atom Transfer; Oxazoles; Oxidative annulation; Photocatalysis

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A novel method for the synthesis of various trisubstituted oxazoles (28 examples, up to 88% yield) has been developed using 9H-thioxanthen-9-one (TX) mediated oxidative annulation of N-acetyl enamide under visible light irradiation in the presence of BF3 center dot Et2O (2.0 equiv) and 40 mol% of PhNO2. This metal-free procedure offers high atom and step economy, environmentally friendly and mild conditions, and a broad range of applicable substrates.
A novel approach to various trisubstituted oxazoles (28 examples, up to 88% yield) has been developed via 9H-thioxanthen-9-one (TX) mediated oxidative annulation of N-acetyl enamide under visible light irradiation in the presence of BF3 center dot Et2O (2.0 equiv) and 40 mol% of PhNO2. This metal-free procedure features high atom and step economy, green and mild conditions and broad substrate scope.

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