Visible‐Light‐Mediated Hydro‐Pentafluoroethylation of Terminal Alkenes With Chloropentafluoroethane

Direct utilization of fluorocarbon feedstocks as fluoroalkyl radical precursors provides an attractive approach to value‐added organofluorine compounds, yet selective activation of their fluorine‐deactivated C─Cl bonds remains challenging. Herein, we report a visible‐light‐driven, metal‐free hydro‐pentafluoroethylation of terminal alkenes using chloropentafluoroethane (CFC‐115, R‐115) directly as the C 2 F 5 source. A trimethylamine–borane‐mediated halogen atom transfer strategy enables efficient activation of the strong C─Cl bond of R‐115 under mild conditions, generating pentafluoroethyl radicals for subsequent alkene functionalization. Terminal alkenes furnished the corresponding C 2 F 5 ‐substituted products in 60%–98% isolated yield, and a 5.0 mmol reaction delivered gram‐scale amount of product in 69% yield. This work establishes regulated R‐115 as a viable pentafluoroethyl radical precursor and illustrates a visible‐light strategy for converting a fluorocarbon feedstock into value‐added organofluorine compounds.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-09-28
DOI
https://doi.org/10.1002/ejoc.70872
Primary Topic
Fluorine in Organic Chemistry
Type
article
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Visible‐Light‐Mediated Hydro‐Pentafluoroethylation of Terminal Alkenes With Chloropentafluoroethane

Jiajia Cheng, Jun Lin, Hongxiang Wang, Chuansen Zhang
European Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Visible‐Light‐Mediated Hydro‐Pentafluoroethylation of Terminal Alkenes With Chloropentafluoroethane

Jiajia Cheng, Jun Lin, Hongxiang Wang, Chuansen Zhang
article en

Abstract

Direct utilization of fluorocarbon feedstocks as fluoroalkyl radical precursors provides an attractive approach to value‐added organofluorine compounds, yet selective activation of their fluorine‐deactivated C─Cl bonds remains challenging. Herein, we report a visible‐light‐driven, metal‐free hydro‐pentafluoroethylation of terminal alkenes using chloropentafluoroethane (CFC‐115, R‐115) directly as the C 2 F 5 source. A trimethylamine–borane‐mediated halogen atom transfer strategy enables efficient activation of the strong C─Cl bond of R‐115 under mild conditions, generating pentafluoroethyl radicals for subsequent alkene functionalization. Terminal alkenes furnished the corresponding C 2 F 5 ‐substituted products in 60%–98% isolated yield, and a 5.0 mmol reaction delivered gram‐scale amount of product in 69% yield. This work establishes regulated R‐115 as a viable pentafluoroethyl radical precursor and illustrates a visible‐light strategy for converting a fluorocarbon feedstock into value‐added organofluorine compounds.

European Journal of Organic Chemistry
Fuzhou University (CN)
Openalex Percentile: Top 13%
Fluorine in Organic Chemistry
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