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. 2023 Nov 14;28(22):7577.
doi: 10.3390/molecules28227577.

Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y

Haruko Shibata  1 , Moeko Nakayama  1 , Koto Tagami  1 , Tadashi Kanbara  1 , Tomoko Yajima  1
Affiliations

Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y

Haruko Shibata et al. Molecules. .

Abstract

Fluoroalkyl compounds are widely used, underscoring a pressing need for the development of methods for their synthesis. However, reports on perfluoroalkylation to styrenes have been sparse. In this study, both hydroxy- and hydro-perfluoroalkylation of styrene were achieved using visible light reactions, catalyzed by eosin Y, by selecting appropriate additives and controlling the eosin Y quenching cycle. These reactions are heavy-metal free, use water as the hydroxyl or hydrogen source, and employ inexpensive and readily available reagents.

Keywords: eosin Y; perfluoroalkylation; photoredox catalyst; styrene.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Hydroxy- and hydro-perfluoroalkylation of styrenes using perfluroalkyl halide as a fluorine source.
Scheme 2
Scheme 2
Hydroxy- and hydro-perfluoroalkylation of various styrenes. a Oxidative reaction conditions: Eosin Y (10 mol%), 1 (0.25 mmol), 2, Na2S2O3 (0.25 equiv.), and K2CO3 (2.0 equiv.) in CH3CN/H2O (7.5 mL/1 mL) under an argon atmosphere with 3 h irradiation with white LED light at 25 °C. b Oxidative reaction conditions: Eosin Y (10 mol%), 1 (0.25 mmol), 3 and DIPEA (2.0 equiv.) in CH3CN/H2O (7.5 mL/1 mL) under an argon atmosphere with 3 h irradiation with white LED light at 25 °C.
Scheme 3
Scheme 3
Types of perfluoroalkylation.
Scheme 4
Scheme 4
Proposed mechanism for hydroxy- and hydro-perfluoroalkylation.
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References

    1. Purser S., Moore P.R., Swallow S., Gouverneur V. Fluorine in medicinal chemistry. Chem. Soc. Rev. 2008;37:320–330. doi: 10.1039/B610213C. - DOI - PubMed
    1. Hagmann W.K. The Many Roles for Fluorine in Medicinal Chemistry. J. Med. Chem. 2008;51:4359–4369. doi: 10.1021/jm800219f. - DOI - PubMed
    1. Meanwell N.A. Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design. J. Med. Chem. 2018;61:5822–5880. doi: 10.1021/acs.jmedchem.7b01788. - DOI - PubMed
    1. Inoue M., Sumii Y., Shibata N. Contribution of Organofluorine Compounds to Pharmaceuticals. ACS Omega. 2020;5:10633–10640. doi: 10.1021/acsomega.0c00830. - DOI - PMC - PubMed
    1. Ogawa Y., Tokunaga E., Kobayashi O., Hirai K., Shibata N. Current Contributions of Organofluorine Compounds to the Agrochemical Industry. iScience. 2020;23:101467. doi: 10.1016/j.isci.2020.101467. - DOI - PMC - PubMed

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