Mild copper(I) iodide/β-keto ester catalyzed coupling reactions of styryl bromides with phenols, thiophenols, and imidazoles

被引：38

作者：

Bao, Weiliang ^{[1
]}

Liu, Yunyun ^{[1
]}

Lv, Xin ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2008年 / 12期

关键词：

beta-keto esters; Ullmann coupling reaction; copper catalysis; vinylation;

D O I：

10.1055/s-2008-1067082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and mild vinylation of O-, S-, and N-nucleophiles is reported. Copper(I) iodide/ethyl 2-oxocyclohexanecarboxylate is used as the catalytic system. The protocol tolerates a broad range of functional groups on the substrates, and gives the corresponding aryl styryl ethers, aryl styryl sulfides, and N-styrylimidazoles in moderate to excellent yields as well as with good stereoselectivity.

引用

页码：1911 / 1917

页数：7

共 55 条

[1] A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloadditions of diazo compounds generated in situ [J].

Aggarwal, VK ;

de Vicente, J ;

Bonnert, RV .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5381-5383

[2]

AISCAR BJJ, 2000, Patent No. 1055653

[3]

AISCAR BJJ, 2001, CHEM ABSTR, V134

[4] Synthetic approaches to sterically hindered N-arylimidazoles through copper-catalyzed coupling reactions [J].

Alcalde, E ;

Dinarès, I ;

Rodríguez, S ;

de Miguel, CG .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1637-1643

[5] 4,7-Dimethoxy-1,10-phenanthroline:: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles [J].

Altman, Ryan A. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2006, 8 (13) :2779-2782

[6] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[7] Synthesis of sulfoxides by the hydrogen peroxide induced oxidation of sulfides catalyzed by iron tetrakis(pentafluorophenyl)porphyrin: Scope and chemoselectivity [J].

Baciocchi, E ;

Gerini, MF ;

Lapi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3586-3589

[8] Copper-catalyzed synthesis of vinyl sulfides [J].

Bates, CG ;

Saejueng, P ;

Doherty, MQ ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (26) :5005-5008

[9] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[10] A USEFUL METHOD FOR CONFIGURATIONAL ASSIGNMENT OF VINYL SULFIDES - STEREOCHEMICAL REASSESSMENT OF THE RADICAL-ADDITION OF BENZENETHIOL TO ALKYNES [J].

BENATI, L ;

CAPELLA, L ;

MONTEVECCHI, PC ;

SPAGNOLO, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08) :1035-1038

← 1 2 3 4 5 6 →