Photo-induced oxidant-free oxidative C–H/N–H cross-coupling between arenes and azoles
書誌事項
- 公開日
- 2017-02-01
- 権利情報
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- https://creativecommons.org/licenses/by/4.0
- https://creativecommons.org/licenses/by/4.0
- DOI
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- 10.1038/ncomms14226
- 公開者
- Springer Science and Business Media LLC
説明
<jats:title>Abstract</jats:title><jats:p>Direct cross-coupling between simple arenes and heterocyclic amines under mild conditions is undoubtedly important for C–N bonds construction. Selective C(sp<jats:sup>2</jats:sup>)-H amination is more valuable. Herein we show a selective C(sp<jats:sup>2</jats:sup>)-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<jats:sup>2</jats:sup>)-H bonds, providing a mild route to <jats:italic>N</jats:italic>-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<jats:sup>2</jats:sup>)-H activation, whereas C(sp<jats:sup>3</jats:sup>)-H bonds are unaffected. This study may have significant implications for the functionalization of methylarenes which are sensitive to oxidative conditions.</jats:p>
収録刊行物
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- Nature Communications
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Nature Communications 8 (1), 14226-, 2017-02-01
Springer Science and Business Media LLC