Pd/Cu-Catalyzed Oxidative C-H Alkenylation of Imidazo[1,2-a]pyridines

被引：58

作者：

Koubachi, Jamal ^{[1
,2
]}

Berteina-Raboin, Sabine ^{[1
]}

Mouaddib, Abderrahim ^{[2
]}

Guillaumet, Gerald ^{[1
]}

机构：

[1] Univ Orleans, CNRS, UMR 6005, Inst Chim Organ & Analyt, F-45067 Orleans 2, France

[2] Univ Sultan Moulay Slimane, Fac Sci & Tech Beni Mellal, Beni Mellal 23000, Morocco

来源：

SYNTHESIS-STUTTGART | 2009年 / 02期

关键词：

palladium/copper-catalyzed oxidative coupling; alkenylation; imidazo[1,2-a]pyridines; DIRECT ARYLATION; BOND FORMATION; PALLADIUM; FUNCTIONALIZATION; HETEROCYCLES; ACTIVATION; ANNULATION; INHIBITORS; CHEMISTRY; DIOXYGEN;

D O I：

10.1055/s-0028-1083252

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel direct and regioselective Pd/Cu-catalyzed intermolecular oxidative coupling of imidazo[1,2-a]pyridines with alkenes was successfully developed. The scope and limitations of the reaction were further studied by using various alkenes. This method provides a 'green' route to 3-alkenylimidazo[1,2-a]pyridine derivatives in high yields.

引用

页码：271 / 276

页数：6

共 47 条

[1] 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

[2]

Anaflous A., 2004, LETT DRUG DES DISCOV, V1, P224, DOI [10.2174/1570180043398885, DOI 10.2174/1570180043398885]

[3]

BADGER A, 1990, Patent No. 9100092

[4] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[5] Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].

Beck, EM ;

Grimster, NP ;

Hatley, R ;

Gaunt, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529

[6]

Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a

[7] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].

Campeau, LC ;

Fagnou, K .

CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264

[8] Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles [J].

Capito, E ;

Brown, JM ;

Ricci, A .

CHEMICAL COMMUNICATIONS, 2005, (14) :1854-1856

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

Cerna, Igor ;

Pohl, Radek ;

Hocek, Michal .

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

[10] Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides [J].

Chiong, Hendrich A. ;

Daugulis, Olafs .

ORGANIC LETTERS, 2007, 9 (08) :1449-1451

← 1 2 3 4 5 →