Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines

被引：428
作者：
Saidi, Ourida [1 ]
Marafie, Jameel [1 ]
Ledger, Araminta E. W. [1 ]
Liu, Po Man [1 ]
Mahon, Mary F. [1 ]
Kociok-Koehn, Gabriele [1 ]
Whittlesey, Michael K. [1 ]
Frost, Christopher G. [1 ]
机构：
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 48期
基金：
英国工程与自然科学研究理事会;
关键词：
C-H BONDS; CROSS-COUPLING REACTIONS; CARBON-HYDROGEN BONDS; DIRECT ARYLATION; ORGANOMETALLIC COMPLEXES; DIRECT FUNCTIONALIZATION; ARYL CHLORIDES; ACTIVATION; PALLADIUM; ARENES;
D O I：
10.1021/ja208286b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：19298 / 19301
页数：4
相关论文
共 66 条
  • [1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
    Ackermann, Lutz
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
  • [2] Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines
    Ackermann, Lutz
    Hofmann, Nora
    Vicente, Ruben
    [J]. ORGANIC LETTERS, 2011, 13 (07) : 1875 - 1877
  • [3] Mechanistic Insight into Direct Arylations with Ruthenium(II) Carboxylate Catalysts
    Ackermann, Lutz
    Vicente, Ruben
    Potukuchi, Harish K.
    Pirovano, Valentina
    [J]. ORGANIC LETTERS, 2010, 12 (21) : 5032 - 5035
  • [4] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [5] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [6] Diethyl carbonate as a solvent for ruthenium catalysed C-H bond functionalisation
    Arockiam, Percia
    Poirier, Valentin
    Fischmeister, Cedric
    Bruneau, Christian
    Dixneuf, Pierre H.
    [J]. GREEN CHEMISTRY, 2009, 11 (11) : 1871 - 1875
  • [7] C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) Systems
    Arockiam, Percia B.
    Fischmeister, Cedric
    Bruneau, Christian
    Dixneuf, Pierre H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) : 6629 - 6632
  • [8] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
    Beletskaya, Irina P.
    Ananikov, Valentine P.
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1596 - 1636
  • [9] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances
    Bellina, F
    Carpita, A
    Rossi, R
    [J]. SYNTHESIS-STUTTGART, 2004, (15): : 2419 - 2440
  • [10] Mechanistic Study of Acetate-Assisted C-H Activation of 2-Substituted Pyridines with [MCl2CP*]2 (M = Rh, Ir) and [RuCl2(p-cymene)]2
    Boutadla, Youcef
    Al-Duaij, Omar
    Davies, David L.
    Griffith, Gerald A.
    Singh, Kuldip
    [J]. ORGANOMETALLICS, 2009, 28 (02) : 433 - 440
1234567