Phosphine-Mediated Photocatalytic Defluorinative Reductive Coupling of Alkynes and Trifluoromethyl Alkenes

Abstract The reductive coupling of alkynes and alkenes has emerged as a straightforward protocol for C–C bond formation from readily available feedstocks. Herein, we report a phosphine-mediated photocatalytic defluorinative reductive coupling of alkynes and trifluoromethyl alkenes with water as the hydrogen source, delivering a range of valuable gem-difluoroalkenes with excellent chemoselectivity under mild conditions. This strategy is gram-scale and can be applied for several pharmaceutical and natural product derivatives. Control experiments and spectroscopic analyses were conducted to probe the underpinning mechanism.

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Publication Details

Journal
Organic Letters
Published
2026-09-04
DOI
https://doi.org/10.1021/acs.orglett.6c03144
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Phosphine-Mediated Photocatalytic Defluorinative Reductive Coupling of Alkynes and Trifluoromethyl Alkenes

Xiaochen Ji, Huawen Huang, Jun Ying, Dongfang Jiang et al.
Organic Letters
Fluorine in Organic Chemistry
article

Phosphine-Mediated Photocatalytic Defluorinative Reductive Coupling of Alkynes and Trifluoromethyl Alkenes

Xiaochen Ji, Huawen Huang, Jun Ying, Dongfang Jiang, Yihong Li, Linqing Ding
article en

Abstract

Abstract The reductive coupling of alkynes and alkenes has emerged as a straightforward protocol for C–C bond formation from readily available feedstocks. Herein, we report a phosphine-mediated photocatalytic defluorinative reductive coupling of alkynes and trifluoromethyl alkenes with water as the hydrogen source, delivering a range of valuable gem-difluoroalkenes with excellent chemoselectivity under mild conditions. This strategy is gram-scale and can be applied for several pharmaceutical and natural product derivatives. Control experiments and spectroscopic analyses were conducted to probe the underpinning mechanism.

Organic Letters
Zhejiang Sci-Tech University (CN), Changsha Medical University (CN), Xiangtan University (CN)
Education Department of Hunan Province, National Natural Science Foundation of China, Natural Science Foundation of Hunan Province
Openalex Percentile: Top 12%
Fluorine in Organic Chemistry
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