CsCF3B(OMe)3: A Versatile Nucleophilic Source of the Trifluoromethyl Anion

Aurélien Dupeux; Andrew G. Durant; Karolina Rabeda; Bijan Mirabi; Austin D. Marchese; Russell F. Algera; Sebastien Monfette; Philipp C. Roosen; Mark Lautens

doi:10.1055/s-0043-1775439

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(07): 1355-1365
DOI: 10.1055/s-0043-1775439

paper

CsCF₃B(OMe)₃: A Versatile Nucleophilic Source of the Trifluoromethyl Anion

Aurélien Dupeux‡

^aDepartment of Chemistry, Davenport Research Laboratories, University of Toronto, Toronto, Ontario M5S 3H6, Canada

,

Andrew G. Durant ‡

^aDepartment of Chemistry, Davenport Research Laboratories, University of Toronto, Toronto, Ontario M5S 3H6, Canada

,

Karolina Rabeda‡

^aDepartment of Chemistry, Davenport Research Laboratories, University of Toronto, Toronto, Ontario M5S 3H6, Canada

,

Bijan Mirabi

^aDepartment of Chemistry, Davenport Research Laboratories, University of Toronto, Toronto, Ontario M5S 3H6, Canada

,

Austin D. Marchese

^aDepartment of Chemistry, Davenport Research Laboratories, University of Toronto, Toronto, Ontario M5S 3H6, Canada

,

Russell F. Algera

^bPfizer Chemical Research and Development, Pfizer Inc., Groton, Connecticut 06340, USA

,

Sebastien Monfette

^bPfizer Chemical Research and Development, Pfizer Inc., Groton, Connecticut 06340, USA

,

Philipp C. Roosen

^bPfizer Chemical Research and Development, Pfizer Inc., Groton, Connecticut 06340, USA

,

Mark Lautens ∗

^aDepartment of Chemistry, Davenport Research Laboratories, University of Toronto, Toronto, Ontario M5S 3H6, Canada

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Abstract

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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 solvents

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Referenzen

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