Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines

Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines

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–Caryl σ bond that induces a strong para-directing effect. Electrophilic...

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Veröffentlicht in:Journal of the American Chemical Society 2011-12, Vol.133 (48), p.19298-19301
Hauptverfasser: Saidi, Ourida, Marafie, Jameel, Ledger, Araminta E. W, Liu, Po Man, Mahon, Mary F, Kociok-Köhn, Gabriele, Whittlesey, Michael K, Frost, Christopher G
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Pyridines - chemistry
Ruthenium - chemistry
Sulfinic Acids - chemistry
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Zusammenfassung: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–Caryl 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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja208286b