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Issue 28, 2017
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α-Halo carbonyls enable meta selective primary, secondary and tertiary C–H alkylations by ruthenium catalysis

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Abstract

A catalytic meta selective C–H alkylation of arenes is described using a wide range of α-halo carbonyls as coupling partners. Previously unreported primary alkylations with high meta selectivity have been enabled by this methodology whereas using straight chain alkyl halides affords ortho substituted products. Mechanistic analysis reveals an activation pathway whereby cyclometalation with a ruthenium(II) complex activates the substrate molecule and is responsible for the meta selectivity observed. A distinct second activation of the coupling partner allows site selective reaction between both components.

Graphical abstract: α-Halo carbonyls enable meta selective primary, secondary and tertiary C–H alkylations by ruthenium catalysis

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Publication details

The article was received on 16 May 2017, accepted on 24 Jun 2017 and first published on 26 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01192J
Citation: Org. Biomol. Chem., 2017,15, 5993-6000
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    α-Halo carbonyls enable meta selective primary, secondary and tertiary C–H alkylations by ruthenium catalysis

    A. J. Paterson, C. J. Heron, C. L. McMullin, M. F. Mahon, N. J. Press and C. G. Frost, Org. Biomol. Chem., 2017, 15, 5993
    DOI: 10.1039/C7OB01192J

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