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Review

Tetramethylammonium Fluoride: Fundamental Properties and Applications in C-F Bond-Forming Reactions and as a Base

1
Department of Chemistry, Faculty of Science, University of Helsinki, P.O. Box 55, 00014 Helsinki, Finland
2
VTT Technical Research Centre of Finland Ltd., P.O. Box 1000, FI-02044 Espoo, Finland
*
Authors to whom correspondence should be addressed.
Academic Editors: Bojan Božić and Jelena Ladjarević
Catalysts 2022, 12(2), 233; https://doi.org/10.3390/catal12020233
Received: 14 January 2022 / Revised: 14 February 2022 / Accepted: 15 February 2022 / Published: 18 February 2022
(This article belongs to the Special Issue Organohalogen Chemistry and Catalysis)
Nucleophilic ionic sources of fluoride are essential reagents in the synthetic toolbox to access high added-value fluorinated building blocks unattainable by other means. In this review, we provide a concise description and rationale of the outstanding features of one of these reagents, tetramethylammonium fluoride (TMAF), as well as disclosing the different methods for its preparation, and how its physicochemical properties and solvation effects in different solvents are intimately associated with its reactivity. Furthermore, herein we also comprehensively describe its historic and recent utilization, up to December 2021, in C-F bond-forming reactions with special emphasis on nucleophilic aromatic substitution fluorinations with a potential sustainable application in industrial settings, as well as its use as a base capable of rendering unprecedented transformations. View Full-Text
Keywords: tetramethylammonium fluoride; TMAF; solvation effects; nucleophilic fluorination; sustainable industrial fluorination; SNAr; [18F]-radiolabelling; superbases; selective methylation; fluorinated excited species tetramethylammonium fluoride; TMAF; solvation effects; nucleophilic fluorination; sustainable industrial fluorination; SNAr; [18F]-radiolabelling; superbases; selective methylation; fluorinated excited species
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MDPI and ACS Style

Iashin, V.; Wirtanen, T.; Perea-Buceta, J.E. Tetramethylammonium Fluoride: Fundamental Properties and Applications in C-F Bond-Forming Reactions and as a Base. Catalysts 2022, 12, 233. https://doi.org/10.3390/catal12020233

AMA Style

Iashin V, Wirtanen T, Perea-Buceta JE. Tetramethylammonium Fluoride: Fundamental Properties and Applications in C-F Bond-Forming Reactions and as a Base. Catalysts. 2022; 12(2):233. https://doi.org/10.3390/catal12020233

Chicago/Turabian Style

Iashin, Vladimir, Tom Wirtanen, and Jesus E. Perea-Buceta. 2022. "Tetramethylammonium Fluoride: Fundamental Properties and Applications in C-F Bond-Forming Reactions and as a Base" Catalysts 12, no. 2: 233. https://doi.org/10.3390/catal12020233

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