Carbonates: eco-friendly solvents for palladium-catalysed direct arylation of heteroaromatics

被引:99
作者
Dong, Jia Jia [1 ]
Roger, Julien [1 ]
Verrier, Cecile [2 ,3 ]
Martin, Thibaut [2 ,3 ]
Le Goff, Ronan [1 ]
Hoarau, Christophe [2 ,3 ]
Doucet, Henri [1 ]
机构
[1] Univ Rennes 1 Catalyse & Organometall, CNRS, Inst Sci Chim Rennes, UMR 6226, F-35042 Rennes, France
[2] Univ Rouen, F-76131 Mont St Aignan, France
[3] INSA, CNRS, Inst Chim Organ Fine IRCOF Associee, UMR 6014, F-76131 Mont St Aignan, France
关键词
DIRECT C-2 ARYLATION; INCLUDING FREE (NH)-IMIDAZOLE; CROSS-COUPLING REACTIONS; C-H FUNCTIONALIZATION; DIMETHYL CARBONATE; ROOM-TEMPERATURE; ARYL HALIDES; REGIOSELECTIVE SYNTHESIS; ALTERNATIVE SOLVENTS; PROPYLENE CARBONATE;
D O I
10.1039/c0gc00229a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The palladium-catalysed direct 2-, 4- or 5-arylation of a wide range of heteroaromatics with aryl halides proceed in moderate to good yields using the eco-friendly solvents carbonates. The best yields were obtained using benzoxazole or thiazole derivatives. The arylation of furan, thiophene, pyrrole, imidazole or isoxazole derivatives was found to require a more elevated reaction temperature.
引用
收藏
页码:2053 / 2063
页数:11
相关论文
共 86 条
  • [1] 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
  • [2] Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C-H Bond Cleavages in the Presence of Air
    Ackermann, Lutz
    Vicente, Ruben
    [J]. ORGANIC LETTERS, 2009, 11 (21) : 4922 - 4925
  • [3] AKITA Y, 1985, HETEROCYCLES, V23, P2327
  • [4] 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
  • [5] Pd-mediated C-H arylation of EDOT and synthesis of push-pull systems incorporating EDOT
    Amaladass, P.
    Clement, J. Arul
    Mohanakrishnan, Arasambattu K.
    [J]. TETRAHEDRON, 2007, 63 (41) : 10363 - 10371
  • [6] Anastas P. T., 2010, Handbook of green chemistry: green solvents
  • [7] AOYAGI Y, 1992, HETEROCYCLES, V33, P257
  • [8] 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
  • [9] Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
    Bahrami, Kiumars
    Khodaei, M. Mehdi
    Naali, Fardin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) : 6835 - 6837
  • [10] Direct arylation of Thiophenes via palladium-catalysed C-H functionalisation at low catalyst loadings
    Battace, Ahmed
    Lemhadri, Mhamed
    Zair, Touriya
    Doucet, Henri
    Santelli, Maurice
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (16) : 2507 - 2516