Oxidative trifluoromethylselenolation of 1,3-dicarbonyls with [Me4N][SeCF3]

Abstract

Reactions of 1,3-ketoesters, -diesters, -diketones, and -ketoamides with [Me₄N][SeCF₃] in the presence of an appropriate oxidant provided a series of 2-trifluoromethylselenolated 1,3-dicarbonyls in moderate to good yields. The trifluoromethylselenolation featured simplicity, mildness, high efficiency, transition-metal-free conditions, and compatibility of various oxidants, and represented the first oxidative trifluoromethylselenolation of 1,3-dicarbonyl compounds with [Me₄N][SeCF₃]. This protocol was also applicable to the oxidative trifluoromethylthiolation of 1,3-dicarbonyls with [Me₄N][SCF₃]/NCS, and oxidative trifluoromethylchalcogenation with nucleophilic XCF₃ (X = O, S, and Se) reagents were compared. The results demonstrated that these nucleophilic XCF₃ salts showed different reaction profiles towards 1,3-dicarbonyls under oxidation conditions.