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Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines


Reference:

Saidi, O., Marafie, J., Ledger, A. E. W., Liu, P. M., Mahon, M. F., Kociok-Kohn, G., Whittlesey, M. K. and Frost, C. G., 2011. Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines. Journal of the American Chemical Society, 133 (48), pp. 19298-19301.

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    Official URL:

    http://dx.doi.org/10.1021/ja208286b

    Abstract

    A selective catalytic meta sulfonation of 2-phenylpyridines was found to occur in the presence of (arene)ruthenium(II) complexes upon reaction with sulfonyl chlorides. The 2-pyridyl group facilitates the formation of a stable Ru-C(aryl) sigma bond that induces a strong para-directing effect. Electrophilic aromatic substitution proceeds with the sulfonyl chloride to furnish a sulfone at the position meta to the chelating group. This new catalytic process offers access to atypical regioselectivity for reactions involving chelation-assisted cyclometalation.

    Details

    Item Type Articles
    CreatorsSaidi, O., Marafie, J., Ledger, A. E. W., Liu, P. M., Mahon, M. F., Kociok-Kohn, G., Whittlesey, M. K. and Frost, C. G.
    DOI10.1021/ja208286b
    DepartmentsFaculty of Science > Chemistry
    Publisher StatementFrost_JACS_2011_133_48_19298.pdf: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ja208286b
    RefereedYes
    StatusPublished
    ID Code27992

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