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

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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.

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

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Article information


Submitted
17 Jan 2020
Accepted
11 Feb 2020
First published
12 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

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

K. Tan, T. Dong, X. Zhang and C. Zhang, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00108B

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