Visible-light photoredox-catalyzed coupling of alkylsulfones with α-(trifluoromethyl)styrenes
Abstract
The synthesis of gem-difluoroalkenes by photocatalytic desulfonylative coupling of alkylsulfones with α-(trifluoromethyl)styrenes is described. Photoredox Ir complex was found to be an effective catalyst for this transformation through single electron reduction of alkyl 1-phenyltetrazolyl sulfones, providing structurally diverse gem-difluoroalkene products in good yields. The resulting alkenes could be further converted into fluorinated derivatives, highlighting the potential utility of this method in the synthesis of organofluorine compounds.
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Supplementary material
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Information & Authors
Information
Published In
Canadian Journal of Chemistry
Volume 101 • Number 7 • July 2023
Pages: 491 - 496
History
Received: 20 October 2022
Accepted: 6 January 2023
Accepted manuscript online: 5 April 2023
Version of record online: 5 May 2023
Notes
This paper is part of a special issue in honour of Cathleen Crudden.
Copyright
© 2023 The Author(s). Permission for reuse (free in most cases) can be obtained from copyright.com.
Data Availability Statement
Materials and methods, experimental procedures, and NMR spectra are available in the Supplementary Information.
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Authors
Author Contributions
Conceptualization: MN
Data curation: YT, MN
Formal analysis: YT, MN
Funding acquisition: MN
Investigation: MN
Methodology: KG, MN
Project administration: MN
Supervision: MN
Validation: MN
Writing – original draft: MN
Writing – review & editing: MN
Competing Interests
The authors declare no competing financial interest.
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Cite As
Yasuyo Tahara, Koushik Ghosh, and Masakazu Nambo. 2023. Visible-light photoredox-catalyzed coupling of alkylsulfones with α-(trifluoromethyl)styrenes. Canadian Journal of Chemistry.
101(7): 491-496. https://doi.org/10.1139/cjc-2022-0271
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