Journal
NATURE COMMUNICATIONS
Volume 8, Issue -, Pages -Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/ncomms14226
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Funding
- 973 Program [2011CB808600, 2012CB725302, 2013CB834804]
- National Natural Science Foundation of China [21390400, 21272180, 21302148, 2109343, 21402217]
- Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
- Ministry of Science and Technology of China [2012YQ120060]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT1030]
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Direct cross-coupling between simple arenes and heterocyclic amines under mild conditions is undoubtedly important for C-N bonds construction. Selective C(sp(2))-H amination is more valuable. Herein we show a selective C(sp(2))-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(sp(2))-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(sp(2))-H activation, whereas C(sp(3))-H bonds are unaffected. This study may have significant implications for the functionalization of methylarenes which are sensitive to oxidative conditions.
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