C(sp<sup>3</sup>)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow.
basic_science · Level V
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- Record sourced from PubMed, PMID 32631892.
- Also identified by DOI 10.1126/science.abb4688.
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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(sp<sup>3</sup>)-H bond cleavage, barring potential applications in synthetic organic chemistry. Here, we report a general and mild strategy to activate C(sp<sup>3</sup>)-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).