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

Vladimir Iashin; Tom Wirtanen; Jesus E. Perea-Buceta

doi:10.3390/catal12020233

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

Vladimir Iashin^*
, Tom Wirtanen
, Jesus E. Perea-Buceta^*

^*Corresponding author for this work

BA5205 Chemical and polymer synthesis

University of Helsinki

Research output: Contribution to journal › Review Article › peer-review

29 Citations (Scopus)

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 language	English
Article number	233
Number of pages	58
Journal	Catalysts
Volume	12
Issue number	2
DOIs	https://doi.org/10.3390/catal12020233
Publication status	Published - 18 Feb 2022
MoE publication type	A2 Review article in a scientific journal

Funding

Funding: This work was enabled by the financial support received from the Academy of Finland (decision no. 321778). We are also grateful for the support from the Faculty of Science of the University of Helsinki.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 9 Industry, Innovation, and Infrastructure

Keywords

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

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10.3390/catal12020233Licence: CC BY

Cite this

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

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.",

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

author = "Vladimir Iashin and Tom Wirtanen and Perea-Buceta, \{Jesus E.\}",

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AU - Iashin, Vladimir

AU - Wirtanen, Tom

AU - Perea-Buceta, Jesus E.

PY - 2022/2/18

Y1 - 2022/2/18

N2 - 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.

AB - 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.

KW - Fluorinated excited species

KW - Nucleophilic fluorination

KW - SAr

KW - Selective methylation

KW - Solvation effects

KW - Superbases

KW - Sustainable industrial fluorination

KW - Tetramethylammonium fluoride

KW - TMAF

KW - [F]-radiolabelling

UR - https://www.scopus.com/pages/publications/85125085243

U2 - 10.3390/catal12020233

DO - 10.3390/catal12020233

M3 - Review Article

AN - SCOPUS:85125085243

SN - 2073-4344

VL - 12

JO - Catalysts

JF - Catalysts

IS - 2

M1 - 233

ER -

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

Abstract

Funding

UN SDGs

Keywords

Access to Document

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