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. 2020 Jan 24;25(3):508.
doi: 10.3390/molecules25030508.

Visible-light Promoted Atom Transfer Radical Addition-Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-Donor

Wen-Wen Xu  1 , Le Wang  2 , Ting Mao  1 , Jiwei Gu  3 , Xiao-Fei Li  2   4 , Chun-Yang He  1   4
Affiliations

Visible-light Promoted Atom Transfer Radical Addition-Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-Donor

Wen-Wen Xu et al. Molecules. .

Abstract

Here, we describe a mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of an electron donor-acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity, thus providing a facile route for further application in pharmaceuticals and life sciences.

Keywords: DMA.; EDA; fluoroalkyl iodides; fluoroalkylated alkenes; noncovalent interaction.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Atom Transfer Radical Addition−Elimination (ATRE) reaction for the synthesis of fluoroalkylated alkenes a,b. a Reaction conditions (unless otherwise specified): 1 (0.3 mmol, 1.0 equiv), 2 (0.45 mmol, 1.5 equiv), KOAc (0.6 mmol, 2.0 equiv) in anhydrous DMA (2.0 mL), r.t. under Ar, purple LEDs, for 16 h. b Yield of isolated product.
Scheme 2
Scheme 2
Mechanistic investigation. (a) Addition of radical and SET inhibitors. (b) Trapping of intermediates. (c) Optical absorption spectra study. (d) Job’s plot. (e) Control experiment.
Scheme 3
Scheme 3
Proposed Reaction Mechanism.
See this image and copyright information in PMC

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