School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, China.
Org Biomol Chem. 2020 Mar 4;18(9):1769-1779. doi: 10.1039/d0ob00108b.
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.
1,3-二酮、二酯、二酮和酮酰胺与[Me4N][SeCF3]在适当氧化剂存在下的反应，以中等至良好的收率提供了一系列 2-三氟甲基硒化的 1,3-二羰基化合物。三氟甲基硒化反应具有简单、温和、高效、无过渡金属条件以及各种氧化剂的兼容性，代表了[Me4N][SeCF3]对 1,3-二羰基化合物的首次氧化三氟甲基硒化反应。该方案还适用于[Me4N][SCF3]/NCS 对 1,3-二羰基化合物的氧化三氟甲基硫代反应，以及与亲核 XCF3（X = O、S 和 Se）试剂的氧化三氟甲硒化反应。结果表明，这些亲核 XCF3 盐在氧化条件下对 1,3-二羰基化合物表现出不同的反应特性。
