Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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.
See this image and copyright information in PMC

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

LinkOut - more resources