Mechanistic insight into ruthenium catalysed: meta -sulfonation of 2-phenylpyridine

Patricia Marcé, Andrew J. Paterson, Mary F. Mahon, Christopher G. Frost

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The catalytic meta-functionalization of arenes has emerged as an important synthetic methodology in the last decade. We report herein structural and mechanistic studies of the meta-sulfonation of phenylpyridine using ruthenium complexes. Furthermore, we disclose that the catalytically active species does not require the presence of a η6-arene ligand. Furthermore, the novel cycloruthenated phenylpyridine complex tosylated at the para position to the metal has been isolated and fully characterised. Protodemetallation studies suggest that a concerted C-H activation-demetallation process may be involved. Overall, this study provides fundamental insight into the meta-sulfonation phenylpyridine reaction pathway and uncovers new reaction intermediates that will guide the design of new catalytic systems for remote meta-functionalization.

Original languageEnglish
Pages (from-to)7068-7076
Number of pages9
JournalCatalysis Science and Technology
Volume6
Issue number19
DOIs
Publication statusPublished - 7 Oct 2016

Fingerprint

Sulfonation
Ruthenium
Reaction intermediates
Metals
Chemical activation
Ligands
2-phenylpyridine

Cite this

Mechanistic insight into ruthenium catalysed : meta -sulfonation of 2-phenylpyridine. / Marcé, Patricia; Paterson, Andrew J.; Mahon, Mary F.; Frost, Christopher G.

In: Catalysis Science and Technology, Vol. 6, No. 19, 07.10.2016, p. 7068-7076.

Research output: Contribution to journalArticle

@article{d2fa977be2b744608a135bc2301dbad1,
title = "Mechanistic insight into ruthenium catalysed: meta -sulfonation of 2-phenylpyridine",
abstract = "The catalytic meta-functionalization of arenes has emerged as an important synthetic methodology in the last decade. We report herein structural and mechanistic studies of the meta-sulfonation of phenylpyridine using ruthenium complexes. Furthermore, we disclose that the catalytically active species does not require the presence of a η6-arene ligand. Furthermore, the novel cycloruthenated phenylpyridine complex tosylated at the para position to the metal has been isolated and fully characterised. Protodemetallation studies suggest that a concerted C-H activation-demetallation process may be involved. Overall, this study provides fundamental insight into the meta-sulfonation phenylpyridine reaction pathway and uncovers new reaction intermediates that will guide the design of new catalytic systems for remote meta-functionalization.",
author = "Patricia Marc{\'e} and Paterson, {Andrew J.} and Mahon, {Mary F.} and Frost, {Christopher G.}",
year = "2016",
month = "10",
day = "7",
doi = "10.1039/c6cy01254j",
language = "English",
volume = "6",
pages = "7068--7076",
journal = "Catalysis Science and Technology",
issn = "2044-4753",
publisher = "Royal Society of Chemistry",
number = "19",

}

TY - JOUR

T1 - Mechanistic insight into ruthenium catalysed

T2 - meta -sulfonation of 2-phenylpyridine

AU - Marcé, Patricia

AU - Paterson, Andrew J.

AU - Mahon, Mary F.

AU - Frost, Christopher G.

PY - 2016/10/7

Y1 - 2016/10/7

N2 - The catalytic meta-functionalization of arenes has emerged as an important synthetic methodology in the last decade. We report herein structural and mechanistic studies of the meta-sulfonation of phenylpyridine using ruthenium complexes. Furthermore, we disclose that the catalytically active species does not require the presence of a η6-arene ligand. Furthermore, the novel cycloruthenated phenylpyridine complex tosylated at the para position to the metal has been isolated and fully characterised. Protodemetallation studies suggest that a concerted C-H activation-demetallation process may be involved. Overall, this study provides fundamental insight into the meta-sulfonation phenylpyridine reaction pathway and uncovers new reaction intermediates that will guide the design of new catalytic systems for remote meta-functionalization.

AB - The catalytic meta-functionalization of arenes has emerged as an important synthetic methodology in the last decade. We report herein structural and mechanistic studies of the meta-sulfonation of phenylpyridine using ruthenium complexes. Furthermore, we disclose that the catalytically active species does not require the presence of a η6-arene ligand. Furthermore, the novel cycloruthenated phenylpyridine complex tosylated at the para position to the metal has been isolated and fully characterised. Protodemetallation studies suggest that a concerted C-H activation-demetallation process may be involved. Overall, this study provides fundamental insight into the meta-sulfonation phenylpyridine reaction pathway and uncovers new reaction intermediates that will guide the design of new catalytic systems for remote meta-functionalization.

UR - http://www.scopus.com/inward/record.url?scp=84989332165&partnerID=8YFLogxK

UR - http://dx.doi.org/10.1039/c6cy01254j

U2 - 10.1039/c6cy01254j

DO - 10.1039/c6cy01254j

M3 - Article

AN - SCOPUS:84989332165

VL - 6

SP - 7068

EP - 7076

JO - Catalysis Science and Technology

JF - Catalysis Science and Technology

SN - 2044-4753

IS - 19

ER -