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

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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.
LanguageEnglish
Pages19298-19301
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number48
Early online date2 Nov 2011
DOIs
StatusPublished - 7 Dec 2011

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Sulfonation
Ruthenium
Chelation
Regioselectivity
Sulfones
Substitution reactions
sulfonyl chloride
2-phenylpyridine

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Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines. / Saidi, Ourida; Marafie, J; Ledger, Araminta E W; Liu, Po Man; Mahon, Mary F; Kociok-Kohn, Gabriele; Whittlesey, Michael K; Frost, Christopher G.

In: Journal of the American Chemical Society, Vol. 133, No. 48, 07.12.2011, p. 19298-19301.

Research output: Contribution to journalArticle

Saidi O, Marafie J, Ledger AEW, Liu PM, Mahon MF, Kociok-Kohn G et al. Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines. Journal of the American Chemical Society. 2011 Dec 7;133(48):19298-19301. Available from, DOI: 10.1021/ja208286b
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AU - Kociok-Kohn,Gabriele

AU - Whittlesey,Michael K

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