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

来源：

GREEN CHEMISTRY | 2009年 / 11卷 / 11期

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

页码：1832 / 1846

页数：15

共 62 条

[31] Regioselective palladium-catalyzed arylation of 3-carboalkoxy furan and thiophene [J].

Glover, B ;

Harvey, KA ;

Liu, B ;

Sharp, MJ ;

Tymoschenko, MF .

ORGANIC LETTERS, 2003, 5 (03) :301-304

[32] Palladium-Catalyzed Direct C-4 Arylation of 2,5-Disubstituted Furans with Aryl Bromides [J].

Gottumukkala, Aditya L. ;

Doucet, Henri .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) :2183-2188

[33] Activated aryl chlorides: Useful partners for the coupling with 2-substituted thiazoles in the palladium-catalysed C-H activation/functionalisation reaction [J].

Gottumukkala, Aditya L. ;

Doucet, Henri .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2007, (23) :3629-3632

[34] Regioselective palladium-catalyzed phenylation of ethyl 4-oxazolecarboxylate [J].

Hoarau, C ;

de Kerdaniel, ADF ;

Bracq, N ;

Grandclaudon, P ;

Couture, A ;

Marsais, F .

TETRAHEDRON LETTERS, 2005, 46 (49) :8573-8577

[35] Microwave-assisted palladium-catalyzed direct arylation of 1,4-disubstituted 1,2,3-triazoles with aryl chlorides [J].

Iwasaki, Masayuki ;

Yorimitsu, Hideki ;

Oshima, Koichiro .

CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (11) :1430-1435

[36] Room temperature and phosphine free palladium catalyzed direct C-2 arylation of indoles [J].

Lebrasseur, Nathalie ;

Larrosa, Igor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (10) :2926-2927

[37] Recent advances in direct arylation via palladium-catalyzed aromatic C-H activation [J].

Li, Bi-Jie ;

Yang, Shang-Dong ;

Shi, Zhang-Jie .

SYNLETT, 2008, (07) :949-957

[38]

Li J.J., 2000, PALLADIUM HETEROCYCL

[39] Establishment of Broadly Applicable Reaction Conditions for the Palladium-Catalyzed Direct Arylation of Heteroatom-Containing Aromatic Compounds [J].

Liegault, Benoit ;

Lapointe, David ;

Caron, Laurence ;

Vlassova, Anna ;

Fagnou, Keith .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05) :1826-1834

[40] Synthesis of 5-methylfuro[3,2-c]quinolin-4(5H)-one via palladium-catalysed cyclisation of N-(2-iodophenyl)-N-methyl-3-furamide [J].

Lindahl, Karl-Fredrik ;

Carroll, Anthony ;

Quinn, Ronald J. ;

Ripper, Justin A. .

TETRAHEDRON LETTERS, 2006, 47 (42) :7493-7495

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