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

Vladimir Iashin (Corresponding Author), Tom Wirtanen, Jesus E. Perea-Buceta (Corresponding Author)

Research output: Contribution to journalReview ArticleScientificpeer-review

Abstract

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.

Original languageEnglish
Article number233
Number of pages58
JournalCatalysts
Volume12
Issue number2
DOIs
Publication statusPublished - 18 Feb 2022
MoE publication typeA2 Review article in a scientific journal

Keywords

  • Fluorinated excited species
  • Nucleophilic fluorination
  • SAr
  • Selective methylation
  • Solvation effects
  • Superbases
  • Sustainable industrial fluorination
  • Tetramethylammonium fluoride
  • TMAF
  • [F]-radiolabelling

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