Controlled Defluorinative Carboxylation Cascade of Sterically Hindered CF<sub>3</sub>-Alkenes with Formate Salt via Photocatalysis

A controlled cleavage of double C-F bonds in sterically hindered tetrasubstituted CF<sub>3</sub>-alkenes using formate salt has been achieved through a photoinduced electron transfer approach. Diverse γ-branched multifunctionalized <i>gem</i>-difluoroalkenes and α-fluoroacrylic acids are obtained sequentially via hydrodefluorination and C-F bond carboxylation with good-to-high yields. Precisely controlling the quantity of formate salt and the reaction time is crucial for obtaining divergent defluorinative products. Formate serves as the C1 source, hydrogen donor, and reducing agent.

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Publication Details

Journal
Organic Letters
Published
2025-03-05
DOI
https://doi.org/10.1021/acs.orglett.5c00476
Citations
5
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
3.95

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article

Controlled Defluorinative Carboxylation Cascade of Sterically Hindered CF3-Alkenes with Formate Salt via Photocatalysis

Jian‐Ping Ma, Peng Yang, Haiping Yu, Yaxin Sun et al.
5 citations
Organic Letters
Fluorine in Organic Chemistry
3.95
article

Controlled Defluorinative Carboxylation Cascade of Sterically Hindered CF3-Alkenes with Formate Salt via Photocatalysis

Jian‐Ping Ma, Peng Yang, Haiping Yu, Yaxin Sun, Runze Zhai
article en
5 citations

Abstract

A controlled cleavage of double C-F bonds in sterically hindered tetrasubstituted CF<sub>3</sub>-alkenes using formate salt has been achieved through a photoinduced electron transfer approach. Diverse γ-branched multifunctionalized <i>gem</i>-difluoroalkenes and α-fluoroacrylic acids are obtained sequentially via hydrodefluorination and C-F bond carboxylation with good-to-high yields. Precisely controlling the quantity of formate salt and the reaction time is crucial for obtaining divergent defluorinative products. Formate serves as the C1 source, hydrogen donor, and reducing agent.

Organic LettersVol. 27(10)
Shandong Normal University (CN), Ministry of Education (ME)
National Natural Science Foundation of China, Natural Science Foundation of Shandong Province, Taishan Scholar Project of Shandong Province
Clean water and sanitation
Openalex Percentile: Top 7%
Fluorine in Organic Chemistry
3.95
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Controlled Defluorinative Carboxylation Cascade of Sterically Hindered CF<sub>3</sub>-Alkenes with Formate Salt via Photocatalysis — Jian‐Ping Ma, Peng Yang, et al. · Organic Letters (2025) | TGRS Research Map | TGRS