ArticleJournal of the American Chemical Society2018
Prenyl Praxis: A Method for Direct Photocatalytic Defluoroprenylation.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Enantioselective copper-catalysed defluorinative alkylation of polyfluoroarenes with alkenes and 1,3-dienes.Chemical science · 2026Article
- Deacylative Polyfluoroarylation via C-C Cleavage of Alkyl Ketones.Organic letters · 2025Article
- Synthetic Advantages of Defluorinative C-F Bond Functionalization.Angewandte Chemie (International ed. in English) · 2023Review
- Molecular Sculpting: A Multipurpose Tool for Expedited Access to Various Fluorinated Arenes via Photocatalytic Hydrodefluorination of Benzoates.The Journal of organic chemistry · 2023Article
- Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals.Angewandte Chemie (International ed. in English) · 2021Article
- Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis.Molecules (Basel, Switzerland) · 2021Review
- Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers.Chemical science · 2021Article
- Selective Quadruple C(spiScience · 2020Article
- Base-Promoted C-C Bond Activation Enables Radical Allylation with Homoallylic Alcohols.Journal of the American Chemical Society · 2020Article
- Regioselective Oxidative Arylation of Fluorophenols.Angewandte Chemie (International ed. in English) · 2019Article
- Selective C-F bond carboxylation ofChemical science · 2019Article
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Authors and funding
2 authors.
Funding
Abstract
The prenyl fragment is the quintessential constituent of terpenoid natural products, a diverse family which contains numerous members with diverse biological properties. In contrast, fluorinated and multifluorinated arenes make up an important class of anthropogenic molecules which are highly relevant to material, agricultural, and pharmaceutical industries. While allylation chemistry is well developed, effective prenylation strategies have been less forthcoming. Herein, we describe the photocatalytic defluoroprenylation, a powerful method that provides access to "hybrid molecules" that possess both the functionality of a prenyl group and fluorinated arenes. This approach involves direct prenyl group transfer under very mild conditions, displays excellent functional group tolerance, and includes relatively short reaction times (<4 h), which is the fastest photocatalytic C-F functionalization developed to date. Additionally, the strategy can be extended to include allyl and geranyl (10 carbon fragment) transfers. Another prominent finding is a reagent-dependent switch in regioselectivity of the major product from para to ortho C-F functionalization.
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