From Refrigerant to Reagent: Repurposing HFC-125 into Inorganic and Organic Fluorinating Agents

We report a sustainable and atom-economical strategy to repurpose the refrigerant HFC-125 (CF<sub>3</sub>CF<sub>2</sub>H) into two valuable fluorinating agents: potassium fluoride (KF) and 1,1,2,2-tetrafluoro-<i>N</i>,<i>N</i>-dimethylethylamine (TFEDMA). Treatment of HFC-125 with KHMDS in toluene at low temperature induces deprotonation and β-fluoride elimination, quantitatively generating KF. The resulting crude KF, designated as KF<sub>125</sub>, efficiently promotes a range of nucleophilic fluorination reactions. Simultaneously, the cogenerated tetrafluoroethylene (TFE) is converted into TFEDMA, achieving complete utilization of HFC-125. This dual-reagent platform represents a practical and scalable approach to upcycling fluorinated industrial feedstocks for synthetic applications.

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Publication Details

Journal
Organic Letters
Published
2025-09-29
DOI
https://doi.org/10.1021/acs.orglett.5c03605
Citations
1
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.79
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article

From Refrigerant to Reagent: Repurposing HFC-125 into Inorganic and Organic Fluorinating Agents

Naoyuki Hoshiya, Zhengyu Zhao, Hiroto Iwasaki, Norio Shibata et al.
1 citations
Organic Letters
Fluorine in Organic Chemistry
0.79
article

From Refrigerant to Reagent: Repurposing HFC-125 into Inorganic and Organic Fluorinating Agents

Naoyuki Hoshiya, Zhengyu Zhao, Hiroto Iwasaki, Norio Shibata, Yosuke Kishikawa, S. NAN'YA
article en
1 citations

Abstract

We report a sustainable and atom-economical strategy to repurpose the refrigerant HFC-125 (CF<sub>3</sub>CF<sub>2</sub>H) into two valuable fluorinating agents: potassium fluoride (KF) and 1,1,2,2-tetrafluoro-<i>N</i>,<i>N</i>-dimethylethylamine (TFEDMA). Treatment of HFC-125 with KHMDS in toluene at low temperature induces deprotonation and β-fluoride elimination, quantitatively generating KF. The resulting crude KF, designated as KF<sub>125</sub>, efficiently promotes a range of nucleophilic fluorination reactions. Simultaneously, the cogenerated tetrafluoroethylene (TFE) is converted into TFEDMA, achieving complete utilization of HFC-125. This dual-reagent platform represents a practical and scalable approach to upcycling fluorinated industrial feedstocks for synthetic applications.

Organic LettersVol. 27(40)
Nagoya Institute of Technology (JP), Daikin (Japan) (JP)
Openalex Percentile: Top 23%
Fluorine in Organic Chemistry
0.79
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From Refrigerant to Reagent: Repurposing HFC-125 into Inorganic and Organic Fluorinating Agents — Naoyuki Hoshiya, Zhengyu Zhao, et al. · Organic Letters (2025) | TGRS Research Map | TGRS