Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines
Journal of the American Chemical Society2011Vol. 133(48), pp. 19298–19301
Citations Over TimeTop 10% of 2011 papers
Ourida Saidi, Jameel Marafie, A.E.W. Ledger, Po Man Liu, Mary F. Mahon, Gabriele Kociok‐Köhn, Michael K. Whittlesey, Christopher G. Frost
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.
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