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Visible‐Light‐Mediated Photocatalytic Synthesis of 2‐Substituted Oxazole‐5‐carbaldehydes Promoted by Benzeneseleninic Acid

Laura Abenante, Gabriela Trisch Quadros, Gelson Perin, Claudio Santi, Filipe Penteado, Eder J. Lenardão

2022European Journal of Organic Chemistry14 citationsDOI

Abstract

Abstract Benzeneseleninic acid was used under visible light irradiation (white LEDs) to promote the oxidative cyclization of N ‐propargyl amides to the respective 2‐substituted oxazole‐5‐carbaldehydes. A total of twelve 2‐aryl oxazole‐5‐carbaldehydes, six of them so far unprecedented, were prepared in 30–90 % yield in just 1 hour of reaction at room temperature. No metal catalysts, nor strong oxidants or heating were necessary, making this a mild method to access a valuable class of compounds. The only co‐products are water and diphenyl diselenide, that can be recovered and converted to new benzeneseleninic acid for a new reaction.

Topics & Concepts

OxazoleChemistryCatalysisPhotocatalysisYield (engineering)PhotochemistryVisible spectrumPropargylCombinatorial chemistryOrganic chemistryMedicinal chemistryMaterials scienceMetallurgyOptoelectronicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsOrganoselenium and organotellurium chemistry