Trifluoromethylative and Pentafluoroethylative Heterofunctionalization (C–O, C–S, and C–N) of Alkenes Using Visible Light Photocatalysis

A mild and general method for photoredox-catalyzed trifluoromethylative and pentafluoroethylative heterofunctionalization of alkenes is proposed. In this reaction, the Togni reagent serves as a CF<sub>3</sub>- or CF<sub>2</sub>CF<sub>3</sub>-radical source for the regioselective formation of the C-CF<sub>3</sub> and C-CF<sub>2</sub>CF<sub>3</sub> bonds from alkenes, and additional nucleophiles (O, S, N) provide C-O, C-S, and C-N bonds, respectively. These reactions provide a common gateway to access the fluoroalkylative heterofunctionalization of alkenes.

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Publication Details

Journal
ACS Omega
Published
2024-11-19
DOI
https://doi.org/10.1021/acsomega.4c06017
Citations
4
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.83

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article

Trifluoromethylative and Pentafluoroethylative Heterofunctionalization (C–O, C–S, and C–N) of Alkenes Using Visible Light Photocatalysis

Seongeun Kang, Ye Rin Choi, Ki Bum Hong, Hongchan An et al.
4 citations
ACS Omega
Fluorine in Organic Chemistry
0.83
article

Trifluoromethylative and Pentafluoroethylative Heterofunctionalization (C–O, C–S, and C–N) of Alkenes Using Visible Light Photocatalysis

Seongeun Kang, Ye Rin Choi, Ki Bum Hong, Hongchan An, Joon Hwang
article en
4 citations

Abstract

A mild and general method for photoredox-catalyzed trifluoromethylative and pentafluoroethylative heterofunctionalization of alkenes is proposed. In this reaction, the Togni reagent serves as a CF<sub>3</sub>- or CF<sub>2</sub>CF<sub>3</sub>-radical source for the regioselective formation of the C-CF<sub>3</sub> and C-CF<sub>2</sub>CF<sub>3</sub> bonds from alkenes, and additional nucleophiles (O, S, N) provide C-O, C-S, and C-N bonds, respectively. These reactions provide a common gateway to access the fluoroalkylative heterofunctionalization of alkenes.

ACS OmegaVol. 9(48)
CHA University (KR), Daegu-Gyeongbuk Medical Innovation Foundation (KR)
Korea Institute for Advancement of Technology, CHA University
Openalex Percentile: Top 30%
Fluorine in Organic Chemistry
0.83
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