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Issue 5, 2015
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Olefinic C–H functionalization through radical alkenylation

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Direct olefinic C–H functionalization represents the ideal way of introducing an alkenyl group into organic molecules. A well-known process is the Heck reaction, which involves alkene insertion and β-hydride elimination in the presence of a transition metal. However, the traditional Heck reaction mainly deals with the alkenylation of aryl or vinyl electrophiles. Recent developments have revealed that alkenylation can also be achieved through radical addition to alkenes and following single-electron-transfer (SET) oxidation/elimination. The radical alkenylation pathway allows alkenylation with a variety of carbon-centered radicals and even heteroatom-centered radicals. This tutorial review gives an overview of recent advances in this emerging field.

Graphical abstract: Olefinic C–H functionalization through radical alkenylation

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The article was received on 19 Oct 2014 and first published on 02 Jan 2015

Article type: Tutorial Review
DOI: 10.1039/C4CS00347K
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Chem. Soc. Rev., 2015,44, 1070-1082

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    Olefinic C–H functionalization through radical alkenylation

    S. Tang, K. Liu, C. Liu and A. Lei, Chem. Soc. Rev., 2015, 44, 1070
    DOI: 10.1039/C4CS00347K

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