Journal of the American Chemical Society 2011-12-07

Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines.

Ourida Saidi, Jameel Marafie, Araminta E W Ledger, Po Man Liu, Mary F Mahon, Gabriele Kociok-Köhn, Michael K Whittlesey, Christopher G Frost

Index: J. Am. Chem. Soc. 133(48) , 19298-301, (2011)

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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) σ 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.© 2011 American Chemical Society