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

Research output: Contribution to journalArticle

325 Citations (Scopus)
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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) 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.
Original languageEnglish
Pages (from-to)19298-19301
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number48
Early online date2 Nov 2011
DOIs
Publication statusPublished - 7 Dec 2011

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