C(sp3)–H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow

    • Gabriele Laudadio1*
    • Yuchao Deng1,2,3,*
    • Klaas van der Wal1
    • Davide Ravelli4
    • Manuel Nuño5
    • Maurizio Fagnoni4
    • Duncan Guthrie5
    • Yuhan Sun2,3
    • Timothy Noël1,†
    • 1Micro Flow Chemistry and Synthetic Methodology, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, Eindhoven, Netherlands.
    • 2School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, P. R. China.
    • 3Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201210, P. R. China.
    • 4PhotoGreen Lab, Department of Chemistry, University of Pavia, Pavia 27100, Italy.
    • 5Vapourtec, Fornham St Genevieve, Bury St Edmunds, Suffolk IP28 6TS, UK.
    • Corresponding author. Email: t.noel@tue.nl
    • *These authors contributed equally to this work.

    Direct activation of gaseous hydrocarbons remains a major challenge for the chemistry community. Because of the intrinsic inertness of these compounds, harsh reaction conditions are typically required to enable C(sp3)–H bond cleavage, barring potential applications in synthetic organic chemistry. Here, we report a general and mild strategy to activate C(sp3)–H bonds in methane, ethane, propane, and isobutane through hydrogen atom transfer using inexpensive decatungstate as photocatalyst at room temperature. The corresponding carbon-centered radicals can be effectively trapped by a variety of Michael acceptors, leading to the corresponding hydroalkylated adducts in good isolated yields and high selectivity (38 examples).

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