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

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

^*Corresponding author for this work

Chemistry

University of Bath

Research output: Contribution to journal › Article › peer-review

448 Citations (Scopus)

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.

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

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title = "Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines",

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.",

author = "Ourida Saidi and Jameel Marafie and Ledger, {Araminta E.W.} and Liu, {Po Man} and Mahon, {Mary F.} and Gabriele Kociok-K{\"o}hn and Whittlesey, {Michael K.} and Frost, {Christopher G.}",

year = "2011",

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doi = "10.1021/ja208286b",

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T1 - Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines

AU - Saidi, Ourida

AU - Marafie, Jameel

AU - Ledger, Araminta E.W.

AU - Liu, Po Man

AU - Mahon, Mary F.

AU - Kociok-Köhn, Gabriele

AU - Whittlesey, Michael K.

AU - Frost, Christopher G.

PY - 2011/12/7

Y1 - 2011/12/7

N2 - 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.

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 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.

UR - http://www.scopus.com/inward/record.url?scp=82555187153&partnerID=8YFLogxK

U2 - 10.1021/ja208286b

DO - 10.1021/ja208286b

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C2 - 22047022

AN - SCOPUS:82555187153

SN - 0002-7863

VL - 133

SP - 19298

EP - 19301

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 48

ER -

Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines

Abstract

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