Microwave-assisted palladium-catalyzed direct arylation of 1,4-disubstituted 1,2,3-triazoles with aryl chlorides

被引：104

作者：

Iwasaki, Masayuki ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

Oshima, Koichiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2007年 / 2卷 / 11期

关键词：

arylation; C-C coupling; nitrogen heterocycles; palladium; triazoles;

D O I：

10.1002/asia.200700206

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of 1,4-disubstituted 1,2,3-triazoles with aryl chlorides in the presence of potassium carbonate under palladium catalysis and microwave irradiation at 250 degrees C for 15 min leads to arylation of the triazole at the 5-position. A variety of functional groups, including ester and hydroxy groups, are compatible. The procedure is suitable for the regioselective preparation of trisubstituted triazoles. Microwave irradiation accelerates the reaction, thus allowing the rapid synthesis of trisubstituted triazoles, which are difficult to synthesize selectively.

引用

页码：1430 / 1435

页数：6

共 45 条

[1]

AKITA Y, 1985, HETEROCYCLES, V23, P2327

[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], ANGEW CHEM INT ED

[4] MICROWAVE-ASSISTED ORGANIC-REACTIONS [J].

CADDICK, S .

TETRAHEDRON, 1995, 51 (38) :10403-10432

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

Chiong, Hendrich A. ;

Daugulis, Olafs .

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

[6] Direct Pd-catalyzed arylation of 1,2,3-triazoles [J].

Chuprakov, Stepan ;

Chernyak, Natalia ;

Dudnik, Alexander S. ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2007, 9 (12) :2333-2336

[7] Microwaves in organic synthesis.: Thermal and non-thermal microwave effects [J].

de la Hoz, A ;

Díaz-Ortiz, A ;

Moreno, A .

CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :164-178

[8] Cross-coupling reaction of iodo-1,2,3-triazoles catalyzed by palladium [J].

Deng, J ;

Wu, YM ;

Chen, QY .

SYNTHESIS-STUTTGART, 2005, (16) :2730-2738

[9] (NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes [J].

Diez-Gonzalez, Silvia ;

Correa, Andrea ;

Cavallo, Luigi ;

Nolan, Steven P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (29) :7558-7564

[10]

Dyker G, 2005, HANDBOOK OF C-H TRANSFORMATIONS: APPLICATIONS IN ORGANIC SYNTHESIS, VOL 1, pV

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