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

Linbin Niu, Hong Yi, Shengchun Wang, Tianyi Liu, Jiamei Liu and Aiwen Lei ()
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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

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: 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.

Date: 2017
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DOI: 10.1038/ncomms14226

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