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Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines
Ourida Saidi, J Marafie, Araminta E W Ledger, Po Man Liu, Mary F Mahon, Gabriele Kociok-Kohn, Michael K Whittlesey, Christopher G Frost
OAI: oai:purehost.bath.ac.uk:publications/bc24b21e-fec2-454d-9a01-7d6f51afc750 • DOI: https://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.