Mild and selective α-fluorination of carbonyl compounds (ketones, 1,3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Brønsted-acidic IL [PMIM(SO3H)/OTf] as promoter
Document Type
Article
Publication Date
10-7-2015
Abstract
Structurally diverse ketones, 1,3-diketones, and β-ketoesters, were selectively monofluorinated with Selectfluor (F-TEDA-BF4) (1 equiv) in [BMIM][PF6] as solvent and [PMIM(SO3H)][OTf] as promoter under mild conditions. In selected cases, the monofluorinated products were transformed to the gem-difluoro derivatives by employing an additional equivalent of Selectfluor, and gem-difluoro-derivatives were synthesized directly from the substrates by employing 2 equiv of Selectfluor. The method was extended to monofluorination of representative α-nitroketones and β-ketonitriles using [BMIM][NTf2] without the need for promoters. The described method offers the added advantage of recycling and reuse of the IL solvent. (Chemical Equation Presented).
Publication Title
Tetrahedron Letters
Volume
56
Issue
41
First Page
5495
Last Page
5499
Digital Object Identifier (DOI)
10.1016/j.tetlet.2015.07.084
ISSN
00404039
E-ISSN
18733581
Citation Information
Reddy, & Laali, K. K. (2015). Mild and selective α-fluorination of carbonyl compounds (ketones, 1,3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Brønsted-acidic IL [PMIM(SO3H)/OTf] as promoter. Tetrahedron Letters, 56(41), 5495–5499. https://doi.org/10.1016/j.tetlet.2015.07.084