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Issue 24, 2018
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Cp*Rh(III) catalyzed ortho-halogenation of N-nitrosoanilines by solvent-controlled regioselective C–H functionalization

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Abstract

We present a novel, efficient, and regioselective method for the rhodium-catalyzed direct C–H ortho-halogenation of anilines that involves a removable N-nitroso directing group. This method featured mild reaction conditions, wide substrate scope, good functional group tolerance and satisfactory yields. To maintain the high ortho-regioselectivity and conversion, increasing the steric hindrance of the solvent was critical. Preliminary mechanistic studies suggest that C–H activation may be involved in the rate-determining step.

Graphical abstract: Cp*Rh(iii) catalyzed ortho-halogenation of N-nitrosoanilines by solvent-controlled regioselective C–H functionalization

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Publication details

The article was received on 10 Mar 2018, accepted on 25 May 2018 and first published on 30 May 2018


Article type: Paper
DOI: 10.1039/C8OB00601F
Citation: Org. Biomol. Chem., 2018,16, 4471-4481
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    Cp*Rh(III) catalyzed ortho-halogenation of N-nitrosoanilines by solvent-controlled regioselective C–H functionalization

    Q. Peng, J. Hu, J. Huo, H. Yuan, L. Xu and X. Pan, Org. Biomol. Chem., 2018, 16, 4471
    DOI: 10.1039/C8OB00601F

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