TY - JOUR
T1 - Tetramethylammonium Fluoride
T2 - Fundamental Properties and Applications in C-F Bond-Forming Reactions and as a Base
AU - Iashin, Vladimir
AU - Wirtanen, Tom
AU - Perea-Buceta, Jesus E.
N1 - Funding Information:
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.
Publisher Copyright:
© 2022 by the authors. Licensee MDPI, Basel, Switzerland.
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 - http://www.scopus.com/inward/record.url?scp=85125085243&partnerID=8YFLogxK
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 -
