Switching the Regioselectivity of Direct C-H Arylation of 1,3-Dimethyluracil

被引：36

作者：

Cernova, Miroslava ^{[1
]}

Pohl, Radek ^{[1
]}

Hocek, Michal ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Gilead Sci & IOCB Res Ctr, CR-16610 Prague 6, Czech Republic

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 22期

关键词：

Pyrimidines; C-H arylation; Regioselectivity; Cross-coupling; Copper; PALLADIUM-CATALYZED ARYLATION; ENZYMATIC INCORPORATION; BOND ACTIVATION; COPPER; HETEROCYCLES; DISCOVERY; EFFICIENT; 2,4(5)-DIARYL-1H-IMIDAZOLES; 4(5)-ARYL-1H-IMIDAZOLES; HETEROAROMATICS;

D O I：

10.1002/ejoc.200900586

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An interesting dichotomy in the regioselectivity and mechanism of direct C-H arylation of 1,3-dimethyluracil was observed. Its Pd-catalyzed reactions with diverse aryl halides in the absence of Cul lead preferentially to 5-aryluracils, while reactions in the presence of Cul give 6-aryl derivatives as the major products. Cu-mediated reactions (in the absence of a Pd catalyst) proceed with lower efficiency but give exclusively 6-aryluracil derivatives. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：3698 / 3701

页数：4

共 44 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] 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

[3]

[Anonymous], 2008, Comprehensive Heterocyclic Chemistry III

[4] Highly selective synthesis of 4(5)-aryl-, 2,4(5)-diaryl-, and 4,5-diaryl-1H-imidazoles via Pd-catalyzed direct C-5 arylation of 1-benzyl-1H-imidazole [J].

Bellina, Fabio ;

Cauteruccio, Silvia ;

Di Fiore, Annarita ;

Marchetti, Chiara ;

Rossi, Renzo .

TETRAHEDRON, 2008, 64 (26) :6060-6072

[5] Development and application of effective protocols for the synthesis of arylheteroarenes and biheteroaryls, including bioactive derivatives, by highly regioselective transition metal-catalyzed direct intermolecular arylation reactions of five-membered heteroarenes with (hetero)aryl halides [J].

Bellina, Fabio ;

Cauteruccio, Silvia ;

Rossi, Renzo .

CURRENT ORGANIC CHEMISTRY, 2008, 12 (09) :774-790

[6] Efficient and practical synthesis of 4(5)-Aryl-1H-imidazoles and 2,4(5)-Diaryl-1H-imidazoles via highly selective palladium-catalyzed arylation reactions [J].

Bellina, Fabio ;

Cauteruccio, Silvia ;

Rossi, Renzo .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8543-8546

[7] Aminophenyl- and nitrophenyl-labeled nucleoside triphosphates:: Synthesis, enzymatic incorporation, and electrochemical detection [J].

Cahova, Hana ;

Havran, Ludek ;

Brazdilova, Petra ;

Pivonkova, Hana ;

Pohl, Radek ;

Fojta, Miroslav ;

Hocek, Michal .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2059-2062

[8] Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].

Campeau, Louis-Charles ;

Stuart, David R. ;

Leclerc, Jean-Philippe ;

Bertrand-Laperle, Megan ;

Villemure, Elisia ;

Sun, Ho-Yan ;

Lasserre, Sandrine ;

Guimond, Nicolas ;

Lecavallier, Melanie ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306

[9] Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C-H Arylation Reactions [J].

Cerna, Igor ;

Pohl, Radek ;

Klepetarova, Blanka ;

Hocek, Michal .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :9048-9054

[10] The first direct C-H arylation of purine nucleosides [J].

Cerna, Igor ;

Pohl, Radek ;

Hocek, Michal .

CHEMICAL COMMUNICATIONS, 2007, (45) :4729-4730

← 1 2 3 4 5 →