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Published on: July 28, 2022
Copper-Catalyzed Chemoselective Ring-Opening Hydroselenation and C-H Selenylation of Isoxazol-5-amines
Yuan-Yi Lu1, Junfen Han2, Yu Teng1
1State Key Laboratory of Advanced Drug Delivery and Release Systems, School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, P. R. China.
Abstract:
Copper-catalyzed highly chemoselective transformations of isoxazol-5-amines have been developed. The first ring-opening hydroselenation of isoxazol-5-amines with selenols or RSeSeR/H2O readily delivers 3-amino-2-selenoacrylamides in high yields, while the C-H selenylation of the substrates with diselenides at a low temperature produces 4-selenoisoxazoles with high efficiency. Both protocols demonstrate good functional group compatibility and mild reaction conditions under inexpensive copper catalysis. Mechanistic studies reveal that the presence of an amino group is indispensable for the successful implementation of the reactions.
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