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Sökning: WFRF:(König Burkhard)

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  • Petzold, Daniel, et al. (författare)
  • Visible light mediated synthesis of β chloro ketones from aryl cyclopropanes
  • 2019
  • Ingår i: Angewandte Chemie International Edition. - : John Wiley & Sons. - 1433-7851 .- 1521-3773. ; 58, s. 8577-8580
  • Tidskriftsartikel (refereegranskat)abstract
    • We report the visible light mediated synthesis of β chloro ketones from aryl cyclopropanes, oxygen, hydrochloric acid and nitric acid. The operationally simple and catalyst free method uses cheap standard lab reagents and displays a broad functional group tolerance. Moreover, scale up of the reaction and late stage functionalization of bioactive compounds is possible, providing the opportunity to utilize the cyclopropane ring as a masked β chloro ketone in a reaction sequence. We propose a light‐driven radical chain reaction initiated by the reaction of diluted hydrochloric and nitric acid producing small quantities of molecular chlorine. The mechanistic hypothesis is supported by 18O labelling and UV‐VIS experiments, cyclovoltammetry and several control reactions.
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  • Schmalzbauer, Matthias, et al. (författare)
  • Redox-Neutral Photocatalytic C-H Carboxylation of Arenes and Styrenes with CO2
  • 2020
  • Ingår i: Chem. - : Elsevier BV. - 2451-9308 .- 2451-9294. ; 6:10, s. 2658-2672
  • Tidskriftsartikel (refereegranskat)abstract
    • Carbon dioxide (CO2) is an attractive one-carbon (C1) building block in terms of sustainability and abundance. However, its low reactivity limits applications in organic synthesis as typically high-energy reagents are required to drive transformations. Here, we present a redox-neutral C-H carboxylation of arenes and styrenes using a photocatalytic approach. Upon blue-light excitation, the anthrolate anion photocatalyst is able to reduce many aromatic compounds to their corresponding radical anions, which react with CO2 to afford carboxylic acids. High-throughput screening and computational analysis suggest that a correct balance between electron affinity and nucleophilicity of substrates is essential. This novel methodology enables the carboxylation of numerous aromatic compounds, including many that are not tolerated in classical carboxylation chemistry. Over 50 examples of C-H functionalizations using CO2 or ketones illustrate a broad applicability. The method opens new opportunities for the valorization of common arenes and may find application in late-stage C-H carboxylation.
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