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Issue 8, 2016
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ortho-Selective C–H addition of N,N-dimethyl anilines to alkenes by a yttrium catalyst

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Abstract

The efficient and selective ortho-alkylation of N,N-dimethyl anilines via C–H addition to alkenes was achieved for the first time using a cationic half-sandwich yttrium catalyst. This protocol constitutes a straightforward and atom-economical route for the synthesis of a new family of tertiary aniline derivatives with branched alkyl substituents, which are otherwise difficult to obtain. DFT calculation studies suggest that the interaction between the yttrium atom and the NMe2 group plays an important role and the intramolecular C–H activation through a σ-bond metathesis pathway is the rate-determining step, which is consistent with the experimental KIE observations.

Graphical abstract: ortho-Selective C–H addition of N,N-dimethyl anilines to alkenes by a yttrium catalyst

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Publication details

The article was received on 23 Feb 2016, accepted on 26 Apr 2016 and first published on 26 Apr 2016


Article type: Edge Article
DOI: 10.1039/C6SC00833J
Chem. Sci., 2016,7, 5265-5270
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    ortho-Selective C–H addition of N,N-dimethyl anilines to alkenes by a yttrium catalyst

    G. Song, G. Luo, J. Oyamada, Y. Luo and Z. Hou, Chem. Sci., 2016, 7, 5265
    DOI: 10.1039/C6SC00833J

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