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

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 reacti...

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Main Authors: Haruko Shibata, Moeko Nakayama, Koto Tagami, Tadashi Kanbara, Tomoko Yajima
Format: Article
Language:English
Published: MDPI AG 2023-11-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/28/22/7577
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author Haruko Shibata
Moeko Nakayama
Koto Tagami
Tadashi Kanbara
Tomoko Yajima
author_facet Haruko Shibata
Moeko Nakayama
Koto Tagami
Tadashi Kanbara
Tomoko Yajima
author_sort Haruko Shibata
collection DOAJ
description 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.
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spelling doaj.art-aa9fdb6fd94641bd871c231bee46bb1d2023-11-24T14:58:18ZengMDPI AGMolecules1420-30492023-11-012822757710.3390/molecules28227577Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin YHaruko Shibata0Moeko Nakayama1Koto Tagami2Tadashi Kanbara3Tomoko Yajima4Department of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanDepartment of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanDepartment of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanDepartment of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanDepartment of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanFluoroalkyl 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.https://www.mdpi.com/1420-3049/28/22/7577perfluoroalkylationphotoredox catalyststyreneeosin Y
spellingShingle Haruko Shibata
Moeko Nakayama
Koto Tagami
Tadashi Kanbara
Tomoko Yajima
Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y
Molecules
perfluoroalkylation
photoredox catalyst
styrene
eosin Y
title Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y
title_full Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y
title_fullStr Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y
title_full_unstemmed Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y
title_short Hydroxy- and Hydro-Perfluoroalkylation of Styrenes by Controlling the Quenching Cycle of Eosin Y
title_sort hydroxy and hydro perfluoroalkylation of styrenes by controlling the quenching cycle of eosin y
topic perfluoroalkylation
photoredox catalyst
styrene
eosin Y
url https://www.mdpi.com/1420-3049/28/22/7577
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