Oxidative Trifluoromethylselenolation of 1,3-Dicarbonyls with [Me4N][SeCF3]
Reactions of 1,3-ketoesters, -diesters, -diketones, and -ketoamide with [Me4N][SeCF3] in the presence of a certain 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, which 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, wherein the oxidative trifluoromethylchalcogenation with the nucleophilic XCF3 (X = O, S, Se) reagents were compared. The results demonstrated that these nucleophilic XCF3 salts possessed different reaction profiles towards 1,3-dicarbonyls under the oxidation conditions.
- This article is part of the themed collection: Synthetic methodology in OBC