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

doi:10.1021/ja208286b

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

Department of Chemistry

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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 language	English
Pages (from-to)	19298-19301
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	48
Early online date	2 Nov 2011
DOIs	https://doi.org/10.1021/ja208286b
Publication status	Published - 7 Dec 2011

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This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ja208286b
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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.",

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AU - Saidi, Ourida

AU - Marafie, J

AU - Ledger, Araminta E W

AU - Liu, Po Man

AU - Mahon, Mary F

AU - Kociok-Kohn, Gabriele

AU - Whittlesey, Michael K

AU - Frost, Christopher G

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AB - 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.

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JO - Journal of the American Chemical Society

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ER -

Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines

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A Flow Process for Aminomethylations using Catalysts Supported on Magnetic Nanoparticles

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Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines

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A Flow Process for Aminomethylations using Catalysts Supported on Magnetic Nanoparticles

500 MHZ NMR SPECTROMETER TO SUPPORT ORGANIC, BIO-ORGANIC AND INORGANIC CHEMISTRY

Cite this