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

Gabriele Laudadio (Corresponding author), Yuchao Deng (Corresponding author), Klaas van der Wal, Davide Ravelli, Manuel Nuño, Maurizio Fagnoni, Duncan Guthrie, Yuhan Sun, Timothy Noël

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

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).
Original languageEnglish
Pages (from-to)92-96
Number of pages5
JournalScience
Volume369
Issue number6499
DOIs
Publication statusPublished - 3 Jul 2020

Fingerprint Dive into the research topics of 'C(sp3)–H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow'. Together they form a unique fingerprint.

  • Cite this

    Laudadio, G., Deng, Y., van der Wal, K., Ravelli, D., Nuño, M., Fagnoni, M., Guthrie, D., Sun, Y., & Noël, T. (2020). C(sp3)–H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow. Science, 369(6499), 92-96. https://doi.org/10.1126/science.abb4688