HFIP in organic synthesis

HF Motiwala, AM Armaly, JG Cacioppo… - Chemical …, 2022 - ACS Publications
1, 1, 1, 3, 3, 3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating
solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic …

Hydrofluorination of Alkynes: From (E) to (Z)

R Gauthier, JF Paquin - Chemistry–A European Journal, 2023 - Wiley Online Library
The hydrofluorination of alkynes is an efficient synthetic route to monofluoroalkenes or
difluoroalkanes. Both fluorinated motifs have found applications in medicinal chemistry and …

Biomass-and calcium carbide-based recyclable polymers

SA Metlyaeva, KS Rodygin, KA Lotsman… - Green …, 2021 - pubs.rsc.org
Biomass is a renewable source of valuable feedstock for the chemical industry of the future.
A promising approach to the utilization of valuable components of biomass is the synthesis …

Stereodivergent alkyne hydrofluorination using protic tetrafluoroborates as tunable reagents

R Guo, X Qi, H Xiang, P Geaneotes… - Angewandte Chemie …, 2020 - Wiley Online Library
The discovery of safe, general, and practical procedures to prepare vinyl fluorides from
readily available precursors remains a synthetic challenge. The metal‐free hydrofluorination …

gem‐Difluoroallylation of Aryl Halides and Pseudo Halides with Difluoroallylboron Reagents in High Regioselectivity

S Sakamoto, TW Butcher, JL Yang… - Angewandte Chemie …, 2021 - Wiley Online Library
We report the palladium‐catalyzed gem‐difluoroallylation of aryl halides and pseudo
halides with 3, 3‐difluoroallyl boronates in high yield with high regioselectivity, and we …

Regioselective Electrophilic Addition to Propargylic B(MIDA)s Enabled by β‐Boron Effect

Y Li, ZH Chen, S Lin, Y Liu, J Qian, Q Li… - Advanced …, 2023 - Wiley Online Library
Electrophilic addition reaction to alkynes is of fundamental importance in organic chemistry,
yet the regiocontrol when reacting with unsymmetrical 1, 2‐dialkyl substituted alkynes is …

Stereospecific synthesis of monofluoroalkenes and their deuterated analogues via Ag-catalyzed decarboxylation

X Liu, F Shi, C Jin, B Liu, M Lei, J Tan - Journal of Catalysis, 2022 - Elsevier
Fluorinated organic molecules have found numerous applications in medicinal chemistry, as
the incorporation of fluorine often improve metabolic stability, lipophilicity and bioactivity …

Determination of the Hammett Acidity of HF/Base Reagents

M Longuet, K Vitse, A Martin-Mingot… - Journal of the …, 2024 - ACS Publications
Harnessing the acidity of HF/base reagents is of paramount importance to improve the
efficiency and selectivity of fluorination reactions. Yet, no general method has been reported …

gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu4NBF4 or electrogenerated acid

M Yamaguchi, H Shimao, K Hamasaki… - Beilstein Journal of …, 2024 - beilstein-journals.org
Abstract gem-Difluorination of carbon–carbon triple bonds was conducted using Brønsted
acids, such as Tf 2 NH and TfOH, combined with Bu 4 NBF 4 as the fluorine source. The …

Access to fluorinated dienes through hydrofluorination of 2-En-4-ynoates

Y Xia, AD Charlack, R Guo, NW Wade… - Organic Chemistry …, 2025 - pubs.rsc.org
The hydrofluorination of enynoates has been developed for the synthesis of fluorinated
dienoates. Using a pyridinium tetrafluoroborate salt that is easily prepared on large scale …