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Synthesis 2025; 57(07): 1355-1365
DOI: 10.1055/s-0043-1775439
DOI: 10.1055/s-0043-1775439
paper
CsCF3B(OMe)3: A Versatile Nucleophilic Source of the Trifluoromethyl Anion
We thank the University of Toronto, the Natural Science and Engineering Research Council (NSERC), and Pfizer Inc. for financial support. A.D. thanks MITACS for funding. A.G.D. and B.M. thank NSERC for a CGS-D scholarship. K.R. thanks the University of Toronto – Chemistry Department for scholarship.
Abstract
We have identified cesium trimethoxy(trifluoromethyl)borate [CsCF3B(OMe)3] as a nucleophilic source for the trifluoromethylation of carbonyl compounds. A differentiating characteristic of CsCF3B(OMe)3 is its heightened reactivity in ethereal solvents compared to its potassium analogue, which is typically employed in dimethylformamide. Also, in contrast to the extensively studied Ruppert–Prakash reagent (TMSCF3), CsCF3B(OMe)3 does not require the addition of an exogenous activator. Described herein, we detail the synthesis of CsCF3B(OMe)3 and demonstrate its efficacy in trifluoromethylation across various scaffolds, including methyl ketones, isatin derivatives, and 1,2-acyclic dicarbonyls.
Key words
nucleophilic trifluoromethylation - carbonyls - isatins - 1,2-dicarbonyls - ethereal solventsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775439. Included are the synthesis of starting materials, stability and kinetic studies, 1H/11B/13C{1H}/19F NMR spectra of all compounds and X-ray structure of 1.
- Supporting Information
Publication History
Received: 14 November 2024
Accepted after revision: 24 December 2024
Article published online:
05 February 2025
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