Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water

被引:133
作者
Ackermann, Lutz [1 ]
Pospech, Jola [1 ]
Potukuchi, Harish Kumar [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
关键词
CARBON-CARBON BONDS; BIARYL CONSTRUCTION; ACTIVATION; PALLADIUM; FUNCTIONALIZATION; ETHERS; CLEAVAGE; ARENES; ALKENYLATIONS; ELECTROPHILES;
D O I
10.1021/ol300671y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ruthenium(II) carboxylate complex [Ru(O(2)CMes)(2)(p-cymene)] enabled efficient direct arylations of unactivated C-H bonds with easily available, inexpensive phenols. Extraordinary chemoselectivity of the well-defined ruthenium catalyst set the stage for challenging C-H/C-O bond functionalizations to occur under solvent-free conditions as well as in water, and allowed first direct C-H bond arylations with user-friendly diaryl sulfates as electrophiles.
引用
收藏
页码:2146 / 2149
页数:4
相关论文
共 82 条
  • [31] Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage
    Ackermann, Lutz
    Novak, Petr
    Vicente, Ruben
    Hofmann, Nora
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) : 6045 - 6048
  • [32] Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates
    Ackermann, Lutz
    Althammer, Andreas
    Fenner, Sabine
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) : 201 - 204
  • [33] N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner
    Antoft-Finch, Aurora
    Blackburn, Tom
    Snieckus, Victor
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (49) : 17750 - 17752
  • [34] 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
  • [35] Solvent-free aromatic C-H functionalisation/halogenation reactions
    Bedford, Robin B.
    Engelhart, Jens U.
    Haddow, Mairi F.
    Mitchell, Charlotte J.
    Webster, Ruth L.
    [J]. DALTON TRANSACTIONS, 2010, 39 (43) : 10464 - 10472
  • [36] Solvent free catalytic C-H functionalisation
    Bedford, Robin B.
    Mitchell, Charlotte J.
    Webster, Ruth L.
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (18) : 3095 - 3097
  • [37] Mechanisms of C-H bond activation: rich synergy between computation and experiment
    Boutadla, Youcef
    Davies, David L.
    Macgregor, Stuart A.
    Poblador-Bahamonde, Amalia I.
    [J]. DALTON TRANSACTIONS, 2009, (30) : 5820 - 5831
  • [38] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water"
    Butler, Richard N.
    Coyne, Anthony G.
    [J]. CHEMICAL REVIEWS, 2010, 110 (10) : 6302 - 6337
  • [39] Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls
    Dankwardt, JW
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) : 2428 - 2432
  • [40] Palladium and Copper Catalysis in Regioselective, Intermolecular Coupling of C-H and C-Hal Bonds
    Daugulis, Olafs
    [J]. C-H ACTIVATION, 2010, 292 : 57 - 84