Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines

Ourida Saidi; Jameel Marafie; Araminta E W Ledger; Po Man Liu; Mary F Mahon; Gabriele Kociok-Köhn; Michael K Whittlesey; Christopher G Frost

doi:10.1021/ja208286b

Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines

J Am Chem Soc. 2011 Dec 7;133(48):19298-301. doi: 10.1021/ja208286b. Epub 2011 Nov 9.

Authors

Ourida Saidi¹, Jameel Marafie, Araminta E W Ledger, Po Man Liu, Mary F Mahon, Gabriele Kociok-Köhn, Michael K Whittlesey, Christopher G Frost

Affiliation

¹ Department of Chemistry, University of Bath, Bath BA2 7AY, U.K.

PMID: 22047022
DOI: 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) 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Pyridines / chemistry*
Ruthenium / chemistry*
Sulfinic Acids / chemistry*

Substances

Pyridines
Sulfinic Acids
2-phenylpyridine
sulfonyl chloride
Ruthenium