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
[1]   Palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides using conventional heating [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Born, Robert .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) :741-748
[2]   Synthesis of a sulfahydantoin library [J].
Albericio, F ;
Bryman, LM ;
Garcia, J ;
Michelotti, EL ;
Nicolás, E ;
Tice, CM .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (03) :290-300
[3]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[4]   Use of "homeopathic" ligand-free palladium as catalyst for aryl-aryl coupling reactions [J].
Alimardanov, A ;
de Vondervoort, LSV ;
de Vries, AHM ;
de Vries, JG .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1812-1817
[5]   Pd-mediated C-H arylation of EDOT and synthesis of push-pull systems incorporating EDOT [J].
Amaladass, P. ;
Clement, J. Arul ;
Mohanakrishnan, Arasambattu K. .
TETRAHEDRON, 2007, 63 (41) :10363-10371
[6]   Direct arylation of Thiophenes via palladium-catalysed C-H functionalisation at low catalyst loadings [J].
Battace, Ahmed ;
Lemhadri, Mhamed ;
Zair, Touriya ;
Doucet, Henri ;
Santelli, Maurice .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (16) :2507-2516
[7]   Palladium-catalyzed direct arylation of furans via C-H functionalization at low catalyst loadings [J].
Battace, Ahmed ;
Lemhadri, Mhamed ;
Zair, Touriya ;
Doucet, Henri ;
Santelli, Maurice .
ORGANOMETALLICS, 2007, 26 (03) :472-474
[8]   Microwave-assisted intramolecular cyclization of electron-rich heterocycle derivatives by a palladium-catalyzed coupling reaction [J].
Beccalli, Egle M. ;
Broggini, Glanluig ;
Martinelli, Michela ;
Sottocornolab, Silvia .
SYNTHESIS-STUTTGART, 2008, 1 (01) :136-140
[9]   Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Rossi, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1379-1382
[10]   Regiocontrolled synthesis of 1,2-diaryl-1H-imidazoles by palladium- and copper-mediated direct coupling of 1-aryl-1H-imidazoles with aryl halides under ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Mannina, L ;
Rossi, R ;
Viel, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (03) :693-703