Photocatalytic <i>E</i> → <i>Z</i> isomerization of <i>gem</i>-bromofluoroalkenes: stereoselective synthesis of β-fluorostyrene derivatives

Stereoselective synthesis of β-fluorostyrene derivatives has been achieved. Selective isomerization of <i>gem</i>-bromofluoroalkenyl benzenes bearing various <i>ortho</i>-substituents is enabled by using Ir photocatalysts with high triplet energy. Subsequent one-pot transition-metal (TM)-catalyzed reactions enable pot-economical synthesis of monofluoroalkenes in a stereoselective manner.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-12-19
DOI
https://doi.org/10.1039/d4ob01658k
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Photocatalytic E → Z isomerization of gem-bromofluoroalkenes: stereoselective synthesis of β-fluorostyrene derivatives

Hiroshi Kato, Yoshihito Kayaki, Takashi Koike
Organic & Biomolecular Chemistry
Fluorine in Organic Chemistry
article

Photocatalytic E → Z isomerization of gem-bromofluoroalkenes: stereoselective synthesis of β-fluorostyrene derivatives

Hiroshi Kato, Yoshihito Kayaki, Takashi Koike
article en

Abstract

Stereoselective synthesis of β-fluorostyrene derivatives has been achieved. Selective isomerization of <i>gem</i>-bromofluoroalkenyl benzenes bearing various <i>ortho</i>-substituents is enabled by using Ir photocatalysts with high triplet energy. Subsequent one-pot transition-metal (TM)-catalyzed reactions enable pot-economical synthesis of monofluoroalkenes in a stereoselective manner.

Organic & Biomolecular ChemistryVol. 23(6)
Tokyo Institute of Technology (JP), Nippon Institute of Technology (JP)
Japan Science and Technology Corporation, Ministry of Education, Culture, Sports, Science and Technology, Japan Society for the Promotion of Science
Affordable and clean energy
Openalex Percentile: Top 82%
Fluorine in Organic Chemistry
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