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
[51]   Scope of the Suzuki-Miyaura Cross-Coupling Reactions of Potassium Heteroaryltrifluoroborates [J].
Molander, Gary A. ;
Canturk, Belgin ;
Kennedy, Lauren E. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :973-980
[52]   Palladium-catalyzed perarylation of 3-thiophene- and 3-furancarboxylic acids accompanied by C-H bond cleavage and decarboxylation [J].
Nakano, Masaya ;
Tsurugi, Hayato ;
Satoh, Tetsuya ;
Miura, Masahiro .
ORGANIC LETTERS, 2008, 10 (09) :1851-1854
[53]  
Negishi E., 2002, HDB ORGANOPALLADIU 3, P213
[54]   Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline [J].
Ohnmacht, Stephan A. ;
Mamone, Patrizia ;
Culshaw, Andrew J. ;
Greaney, Michael F. .
CHEMICAL COMMUNICATIONS, 2008, (10) :1241-1243
[55]   Direct Arylations of 2H-Indazoles On Water [J].
Ohnmacht, Stephan A. ;
Culshaw, Andrew J. ;
Greaney, Michael F. .
ORGANIC LETTERS, 2010, 12 (02) :224-226
[56]   PALLADIUM-CATALYZED ARYLATION OF FURAN, THIOPHENE, BENZO[B]FURAN AND BENZO[B]THIOPHENE [J].
OHTA, A ;
AKITA, Y ;
OHKUWA, T ;
CHIBA, M ;
FUKUNAGA, R ;
MIYAFUJI, A ;
NAKATA, T ;
TANI, N ;
AOYAGI, Y .
HETEROCYCLES, 1990, 31 (11) :1951-1958
[57]   ANTIMICROBIALS .1. BENZOTHIAZOLYLBENZYLAMINES [J].
PALMER, PJ ;
HALL, G ;
TRIGG, RB ;
WARRINGTON, JV .
JOURNAL OF MEDICINAL CHEMISTRY, 1971, 14 (12) :1223-+
[58]   Direct arylation reactions catalyzed by Pd(OH)2/C:: Evidence for a soluble palladium catalyst [J].
Parisien, M ;
Valette, D ;
Fagnou, K .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (19) :7578-7584
[59]   Propylene carbonate stabilized nanostructured palladium clusters as catalysts in Heck reactions [J].
Reetz, MT ;
Lohmer, G .
CHEMICAL COMMUNICATIONS, 1996, (16) :1921-1922
[60]   Room-Temperature Direct Arylation of Polyfluorinated Arenes under Biphasic Conditions [J].
Rene, Olivier ;
Fagnou, Keith .
ORGANIC LETTERS, 2010, 12 (09) :2116-2119