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C(sp3)–H sulfinylation of light hydrocarbons with sulfur dioxide via hydrogen atom transfer photocatalysis in flow

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  • Dmitrii Nagornîi

    (University of Amsterdam)

  • Fabian Raymenants

    (University of Amsterdam)

  • Nikolaos Kaplaneris

    (University of Amsterdam)

  • Timothy Noël

    (University of Amsterdam)

Abstract

Sulfur-containing scaffolds originating from small alkyl fragments play a crucial role in various pharmaceuticals, agrochemicals, and materials. Nonetheless, their synthesis using conventional methods presents significant challenges. In this study, we introduce a practical and efficient approach that harnesses hydrogen atom transfer photocatalysis to activate volatile alkanes, such as isobutane, butane, propane, ethane, and methane. Subsequently, these nucleophilic radicals react with SO2 to yield the corresponding sulfinates. These sulfinates then serve as versatile building blocks for the synthesis of diverse sulfur-containing organic compounds, including sulfones, sulfonamides, and sulfonate esters. Our use of flow technology offers a robust, safe and scalable platform for effectively activating these challenging gaseous alkanes, facilitating their transformation into valuable sulfinates.

Suggested Citation

  • Dmitrii Nagornîi & Fabian Raymenants & Nikolaos Kaplaneris & Timothy Noël, 2024. "C(sp3)–H sulfinylation of light hydrocarbons with sulfur dioxide via hydrogen atom transfer photocatalysis in flow," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-49322-w
    DOI: 10.1038/s41467-024-49322-w
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    References listed on IDEAS

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    1. Jiapian Huang & Fei Liu & Ling-Hui Zeng & Shaoyu Li & Zhiyuan Chen & Jie Wu, 2022. "Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce–Smiles rearrangement," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
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