Photocatalytic Dual-Defluorination Thiolation of Trifluoromethyl Hydrazones

The defluorination of trifluoromethyl groups typically involves breaking one or all three C-F bonds, while selectively cleaving exactly two C-F bonds presents a considerable challenge. In this work, we present a method for the sequential defluorination of trifluoromethyl hydrazones under photocatalytic conditions, which involves the specific breakage of two C-F bonds followed by thiolation to yield monofluorinated alkenes containing a thiol group. Transforming trifluoromethyl-containing polyfluoroalkyl substances into fluorinated non-PFAS compounds holds potential practical implications.

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Publication Details

Journal
Organic Letters
Published
2025-05-09
DOI
https://doi.org/10.1021/acs.orglett.5c01492
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Photocatalytic Dual-Defluorination Thiolation of Trifluoromethyl Hydrazones

Jin‐Hong Lin, Wenjie Pan, Weiguo Cao, Ji‐Chang Xiao
Organic Letters
Fluorine in Organic Chemistry
article

Photocatalytic Dual-Defluorination Thiolation of Trifluoromethyl Hydrazones

Jin‐Hong Lin, Wenjie Pan, Weiguo Cao, Ji‐Chang Xiao
article en

Abstract

The defluorination of trifluoromethyl groups typically involves breaking one or all three C-F bonds, while selectively cleaving exactly two C-F bonds presents a considerable challenge. In this work, we present a method for the sequential defluorination of trifluoromethyl hydrazones under photocatalytic conditions, which involves the specific breakage of two C-F bonds followed by thiolation to yield monofluorinated alkenes containing a thiol group. Transforming trifluoromethyl-containing polyfluoroalkyl substances into fluorinated non-PFAS compounds holds potential practical implications.

Organic LettersVol. 27(20)
Shanghai University (CN), Shanghai Institute of Organic Chemistry (CN), Innovative Research (United States) (US), University of Chinese Academy of Sciences (CN)
National Natural Science Foundation of China, Chinese Academy of Sciences, Science and Technology Commission of Shanghai Municipality, National Key Research and Development Program of China
Openalex Percentile: Top 93%
Fluorine in Organic Chemistry
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