Synthesis of 2,5-Diarylpyrroles by Ligand-Free Palladium-Catalyzed CH Activation of Pyrroles in Ionic Liquids

被引：47

作者：

Ehlers, Peter ^{[1
,2
]}

Petrosyan, Andranik ^{[1
,2
,3
]}

Baumgard, Jens ^{[1
,2
]}

Jopp, Stefan ^{[1
,2
]}

Steinfeld, Norbert ^{[2
]}

Ghochikyan, Tariel V. ^{[3
]}

Saghyan, Ashot S. ^{[3
,4
]}

Fischer, Christine ^{[2
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany

[3] Yerevan State Univ, Fac Chem, Yerevan 0025, Armenia

[4] NAS RA, Sci & Prod Ctr Armbiotechnol, Yerevan 0056, Armenia

来源：

CHEMCATCHEM | 2013年 / 5卷 / 08期

关键词：

C-H activation; heterocycles; ionic liquids; nanoparticles; palladium; CROSS-COUPLING REACTIONS; DIRECT ARYLATION; HECK REACTIONS; ARYL BROMIDES; COMPLEXES; POTENT; FUNCTIONALIZATION; DERIVATIVES; MECHANISM; ACIDS;

D O I：

10.1002/cctc.201300099

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The palladium-catalyzed CH activation and arylation of N-methylpyrrole and N-phenylpyrrole allowed a convenient synthesis of diarylpyrroles. The reactions were performed by using tetrabutylammonium acetate as an ionic solvent, which allowed for the application of a ligand-free catalytic system by using simple palladium salts or polyvinylpyrrolidone-stabilized palladium nanoparticles as the catalyst.

引用

页码：2504 / 2511

页数：8

共 75 条

[41]

MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803

[42] Synthesis of mono- and bis-arylated 3,4-(ethylenedioxythiophenes) via direct palladium catalyzed arylation reactions [J].

Mohanakrishnan, Arasambattu K. ;

Amaladass, P. ;

Clement, J. Arul .

TETRAHEDRON LETTERS, 2007, 48 (04) :539-544

[43] Heterocycle Synthesis via Direct C-H/N-H Coupling [J].

Nadres, Enrico T. ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :7-10

[44] Palladium-Catalyzed Indole, Pyrrole, and Furan Arylation by Aryl Chlorides [J].

Nadres, Enrico T. ;

Lazareva, Anna ;

Daugulis, Olafs .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02) :471-483

[45]

NAKAMURA N, 1982, HETEROCYCLES, V17, P235

[46] 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

[47] Synthetic Studies toward the Mannopeptimycins: Synthesis of Orthogonally Protected β-Hydroxyenduracididines [J].

Olivier, Kevin S. ;

Van Nieuwenhze, Michael S. .

ORGANIC LETTERS, 2010, 12 (08) :1680-1683

[48] On the nature of the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings - Homogeneous or heterogeneous catalysis, a critical review [J].

Phan, NTS ;

Van Der Sluys, M ;

Jones, CW .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (06) :609-679

[49] 1,3-diaryl-4,5,6,7-tetrahydro-2H-isoindole derivatives:: A new series of potent and selective COX-2 inhibitors in which a sulfonyl group is not a structural requisite [J].

Portevin, B ;

Tordjman, C ;

Pastoureau, P ;

Bonnet, J ;

De Nanteuil, G .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (24) :4582-4593

[50] 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

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