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Photo-induced oxidant-free oxidative C–H/N–H cross-coupling between arenes and azoles

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  • Linbin Niu

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Hong Yi

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Shengchun Wang

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Tianyi Liu

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Jiamei Liu

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Aiwen Lei

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University
    State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University)

Abstract

Direct cross-coupling between simple arenes and heterocyclic amines under mild conditions is undoubtedly important for C–N bonds construction. Selective C(sp2)-H amination is more valuable. Herein we show a selective C(sp2)-H amination of arenes (alkyl-substituted benzenes, biphenyl and anisole derivatives) accompanied by hydrogen evolution by using heterocyclic azoles as nitrogen sources. The reaction is selective for C(sp2)-H bonds, providing a mild route to N-arylazoles. The KIE (kinetic isotope effect) experiment reveals the cleavage of C–H bond is not involved in the rate-determining step. Kinetic studies indicate the first-order behaviour with respect to the arene component. It is interesting that this system works without the need for any sacrificial oxidant and is highly selective for C(sp2)-H activation, whereas C(sp3)-H bonds are unaffected. This study may have significant implications for the functionalization of methylarenes which are sensitive to oxidative conditions.

Suggested Citation

  • Linbin Niu & Hong Yi & Shengchun Wang & Tianyi Liu & Jiamei Liu & Aiwen Lei, 2017. "Photo-induced oxidant-free oxidative C–H/N–H cross-coupling between arenes and azoles," Nature Communications, Nature, vol. 8(1), pages 1-7, April.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms14226
    DOI: 10.1038/ncomms14226
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