Pd/C-catalyzed cyanation of aryl halides in aqueous PEG

被引：98

作者：

Chen, Gong ^{[1
]}

Weng, Jiang ^{[1
]}

Zheng, Zhanchao ^{[1
]}

Zhu, Xinhai ^{[1
]}

Cai, Yaoyao ^{[1
]}

Cai, Jiwen ^{[1
]}

Wan, Yiqian ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 20期

关键词：

palladium; cyanides; water chemistry; microwaves; sustainable chemistry;

D O I：

10.1002/ejoc.200800295

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An environmentally friendly Pd/C-PEG-H2O system was developed for the cyanation of aryl halides under microwave irradiation. A wide range of aryl bromides, iodides, and some activated chlorides were demonstrated to be cyanated smoothly by using nontoxic K-4[Fe(CN)(6)]center dot 3H(2)O as the cyanide source. There is no phosphorus- or nitrogen-containing ligand or solvent involved. Moreover, this reaction can be carried out without the protection of inert atmosphere. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：3524 / 3528

页数：5

共 45 条

[1] Rapid cyanation of aryl iodides in water using microwave promotion [J].

Arvela, RK ;

Leadbeater, NE ;

Torenius, HM ;

Tye, H .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (07) :1119-1121

[2] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[3] Efficient microwave-assisted cyanation of aryl bromide [J].

Cai, LZ ;

Liu, X ;

Tao, XC ;

Shen, D .

SYNTHETIC COMMUNICATIONS, 2004, 34 (07) :1215-1221

[4] Palladium-free copper-catalyzed coupling reaction of aryl iodides and terminal acetylenes in water [J].

Chen, Gong ;

Zhu, Xinhai ;

Cai, Jiwen ;

Wan, Yiqian .

SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) :1355-1361

[5] Cyanation of aryl chlorides with potassium hexacyanoferrate(II) catalyzed by cyclopalladated ferrocenylimine tricyclohexylphosphine complexes [J].

Cheng, Yi-nan ;

Duan, Zheng ;

Li, Ting ;

Wu, Yangjie .

SYNLETT, 2007, (04) :543-546

[6] A facile microwave-assisted palladium-catalyzed cyanation of aryl chlorides [J].

Chobanian, HR ;

Fors, BP ;

Lin, LS .

TETRAHEDRON LETTERS, 2006, 47 (19) :3303-3305

[7] Microwave-assisted copper-catalyzed sonogashira reaction in PEG solvent [J].

Colacino, Evelina ;

Daich, Latifa ;

Martinez, Jean ;

Lamaty, Frederic .

SYNLETT, 2007, (08) :1279-1283

[8] Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides [J].

Cristau, HJ ;

Ouali, A ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2483-2492

[9] CYANATION OF AROMATIC HALIDES [J].

ELLIS, GP ;

ROMNEYALEXANDER, TM .

CHEMICAL REVIEWS, 1987, 87 (04) :779-794

[10] Novel trans-spanned palladium complexes as efficient catalysts in mild and amine-free cyanation of aryl bromides under air [J].

Grossman, O ;

Gelman, D .

ORGANIC LETTERS, 2006, 8 (06) :1189-1191

← 1 2 3 4 5 →