Highly efficient synthesis of 2,3,4-trisubstituted furans via silver-catalyzed sequential nucleophilic addition and cyclization reactions of haloalkynes

被引：13

作者：

Zeng, Wei ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Sun, Yadong ^{[1
]}

Chen, Zhengwang ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 35期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

Furan; Silver; Haloalkynes; Nucleophilic addition; Cyclization; REGIOSELECTIVE SYNTHESIS; DIRECT ALKYNYLATION; BONDS; ALKYNES; 1,1-DIBROMO-1-ALKENES; BROMOALKYNYLATION; CYCLOADDITION; IMIDAZOLES; HYDRATION; HALIDES;

D O I：

10.1016/j.tetlet.2013.05.140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective synthesis of 2,3,4-trisubstituted furans using AgNO3 catalyst from haloallcynes in a one-pot procedure has been reported. The transformation consists of a sequential silver-catalyzed nucleophilic addition and cyclization reaction of haloalkynes. A wide variety of haloalkynes can be used in this chemical process. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

引用

页码：4605 / 4609

页数：5

共 56 条

[1] TiCl4-Catalyzed indirect anti-markovnikov hydration of alkynes:: Application to the synthesis of benzo[b]furans [J].

Ackermann, Lutz ;

Kaspar, Ludwig T. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6149-6153

[2] Alkynyl halides in ruthenium(II)-catalyzed [2+2] cycloadditions of bicyclic alkenes [J].

Allen, Anna ;

Villeneuve, Karine ;

Cockburn, Neil ;

Fatila, Elisabeth ;

Riddell, Nicole ;

Tam, William .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (24) :4178-4192

[3] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[4] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].

Ano, Yusuke ;

Tobisu, Mamoru ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986

[5] Mechanistic Studies and Improvement of Coinage Metal-Catalyzed Transformation of Alkynyloxiranes to Furans: An Alcohol Addition-Cyclization-Elimination Cascade [J].

Blanc, Aurelien ;

Tenbrink, Katharina ;

Weibel, Jean-Marc ;

Pale, Patrick .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5342-5348

[6] Substituent Effects on the Reversibility of Furan-Maleimide Cycloadditions [J].

Boutelle, Robert C. ;

Northrop, Brian H. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) :7994-8002

[7] Cu-Catalyzed N-Alkynylation of Imidazoles, Benzimidazoles, Indazoles, and Pyrazoles Using PEG as Solvent Medium [J].

Burley, Glenn A. ;

Davies, David L. ;

Griffith, Gerry A. ;

Lee, Michael ;

Singh, Kuldip .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :980-983

[8] Copper-Catalyzed Domino Rearrangement/Dehydrogenation Oxidation/Carbene Oxidation for One-Pot Regiospecific Synthesis of Highly Functionalized Polysubstituted Furans [J].

Cao, Hua ;

Jiang, Huanfeng ;

Yao, Wenjuan ;

Liu, Xiaohang .

ORGANIC LETTERS, 2009, 11 (09) :1931-1933

[9] Furan based cyclic Oligopeptides selectively target G-quadruplex [J].

Chakraborty, Tushar Kanti ;

Arora, Amit ;

Roy, Saumya ;

Kumar, Niti ;

Maiti, Souvik .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (23) :5539-5542

[10] Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes [J].

Chen, Zhengwang ;

Huang, Gao ;

Jiang, Huanfeng ;

Huang, Huawen ;

Pan, Xiaoyan .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (04) :1134-1139

← 1 2 3 4 5 6 →