Low catalyst loading ligand-free palladium-catalyzed direct arylation of furans: an economically and environmentally attractive access to 5-arylfurans

被引:95
作者
Dong, Jia Jia [1 ]
Roger, Julien [1 ]
Pozgan, Franc [2 ]
Doucet, Henri [1 ]
机构
[1] Univ Rennes 1, CNRS, Inst Sci Chim Rennes, UMR Catalyse & Organomet 6226, F-35042 Rennes, France
[2] Univ Ljubljana, Fac Chem & Chem Technol, SI-1000 Ljubljana, Slovenia
关键词
DIRECT C-2 ARYLATION; INCLUDING FREE (NH)-IMIDAZOLE; C-H FUNCTIONALIZATION; REGIOSELECTIVE SYNTHESIS; HETEROARYL HALIDES; ARYLBORONIC ACIDS; ROOM-TEMPERATURE; ARYL CHLORIDES; HECK REACTIONS; DERIVATIVES;
D O I
10.1039/b915290n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The direct 5-arylation of furans at very low catalyst loading using Pd(OAc)(2) as catalyst without added ligand proceed in high yields. Turnover numbers up to 10000 have been obtained for the coupling of several activated aryl bromides. A wide range of functions on the furan or aryl bromide is tolerated.
引用
收藏
页码:1832 / 1846
页数:15
相关论文
共 62 条
[51]   APPLICATION OF SETHPAULVAN-DUYSE EQUATION .3. TRANSMISSION OF POLAR EFFECTS BY FURAN RING [J].
PERJESSY, A ;
KRUTOSIKOVA, A ;
OLEJNIK, AF .
TETRAHEDRON, 1975, 31 (23) :2936-2939
[52]   Ligand-free palladium-catalysed direct arylation of heteroaromatics using low catalyst loadings [J].
Pozgan, Franc ;
Roger, Julien ;
Doucet, Henri .
CHEMSUSCHEM, 2008, 1 (05) :404-407
[53]   Ligand-free Heck reactions using low Pd-loading [J].
Reetz, MT ;
de Vries, JG .
CHEMICAL COMMUNICATIONS, 2004, (14) :1559-1563
[54]  
RIBEREAU P, 1975, CR ACAD SCI C CHIM, V280, P293
[55]   Aryl triflates:: useful coupling partners for the direct arylation of heteroaryl derivatives via Pd-catalyzed C-H activation-functionalization [J].
Roger, Julien ;
Doucet, Henri .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (01) :169-174
[56]   Ligand-Free Palladium-Catalyzed Direct Arylation of Thiazoles at Low Catalyst Loadings [J].
Roger, Julien ;
Pozgan, Franc ;
Doucet, Henri .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1179-1186
[57]   Ligand-less palladium-catalyzed direct 5-arylation of thiophenes at low catalyst loadings [J].
Roger, Julien ;
Pozgan, Franc ;
Doucet, Henri .
GREEN CHEMISTRY, 2009, 11 (03) :425-432
[58]   Catalytic direct arylation of heteroaromatic compounds [J].
Satoh, Tetsuya ;
Miura, Masahiro .
CHEMISTRY LETTERS, 2007, 36 (02) :200-205
[59]   Direct transition metal-catalyzed functionalization of heteroaromatic compounds [J].
Seregin, Ilya V. ;
Gevorgyan, Vladimir .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1173-1193
[60]  
Tralic-Kulenovic V, 1998, HETEROCYCL COMMUN, V4, P423