Homocoupling of Terminal Alkynes Catalysed by Ultrafine Copper Nanoparticles on Titania

被引：94

作者：

Alonso, Francisco ^{[1
,2
]}

Melkonian, Taki ^{[1
,2
]}

Moglie, Yanina ^{[1
,2
]}

Yus, Miguel ^{[1
,2
]}

机构：

[1] Univ Alicante, Dept Quim Organ, Fac Ciencias, E-03080 Alicante, Spain

[2] Univ Alicante, ISO, E-03080 Alicante, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 13期

关键词：

Alkynes; C-C coupling; Copper; Nanoparticles; Titanium; Heterogeneous catalysis; 1,3-DIYNES; REDUCTION; GREEN;

D O I：

10.1002/ejoc.201001735

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper nanoparticles on titania effectively catalyse the oxidative homocoupling of terminal alkynes in the presence of piperidine as a base in tetrahydrofuran (THF) or under solvent-free conditions. A wide range of diynes have been synthesised in high yields using low catalyst loading (1 mol-% Cu). The copper catalyst (mainly as Cu2O) has been characterised by different means, is easy to prepare, can be reutilised several times, works either in air or under inert atmosphere and was shown to be superior to other commercially available copper sources.

引用

页码：2524 / 2530

页数：7

共 45 条

[21] Preparation and characterization of Cu2O/TiO2 nano-nano heterostructure photocatalysts [J].

Huang, Lei ;

Peng, Feng ;

Wang, Hongjuan ;

Yu, Hao ;

Li, Zhong .

CATALYSIS COMMUNICATIONS, 2009, 10 (14) :1839-1843

[22] Cu(II)-promoted oxidative homocoupling reaction of terminal alkynes in supercritical carbon dioxide [J].

Jiang, HF ;

Tang, JY ;

Wang, AZ ;

Deng, GH ;

Yang, SR .

SYNTHESIS-STUTTGART, 2006, (07) :1155-1161

[23] Facile Synthesis of Trisubstituted Allenynes by Phosphane-Mediated Deoxygenation of 2,4-Pentadiyn-1-ol [J].

Jiang, Huanfeng ;

Wang, Wei ;

Yin, Biaolin ;

Liu, Weibing .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) :4450-4453

[24]

Kamata K., 2008, ANGEW CHEM, V120, P2441

[25] Efficient oxidative alkyne homocoupling catalyzed by a monomeric dicopper-substituted silicotungstate [J].

Kamata, Keigo ;

Yamaguchi, Syuhei ;

Kotani, Miyuki ;

Yamaguchi, Kazuya ;

Mizuno, Noritaka .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) :2407-2410

[26] Design of high-performance heterogeneous metal catalysts for green and sustainable chemistry [J].

Kaneda, Kiyotomi ;

Ebitani, Kohki ;

Mizugaki, Tomoo ;

Mori, Kohsuke .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2006, 79 (07) :981-1016

[27] Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases [J].

Koradin, C ;

Dohle, W ;

Rodriguez, AL ;

Schmid, B ;

Knochel, P .

TETRAHEDRON, 2003, 59 (09) :1571-1587

[28] Copper-Zeolites as Catalysts for the Coupling of Terminal Alkynes: An Efficient Synthesis of Diynes [J].

Kuhn, Philippe ;

Alix, Aurelien ;

Kumarrajaa, Mayilvasagam ;

Louis, Benoit ;

Pale, Patrick ;

Sommer, Jean .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (03) :423-429

[29] Ligand- and base-free synthesis of 1,3-diynes catalyzed by low loading of heterogeneous Pd/C and cuI [J].

Kurita, Takanori ;

Abe, Masami ;

Maegawa, Tomohiro ;

Monguchi, Yasunari ;

Sajiki, Hironao .

SYNLETT, 2007, (16) :2521-2524

[30] Transmetalation of palladium enolate and its application in palladium-catalyzed homocoupling of alkynes: A room-temperature, highly efficient route to make diynes [J].

Lei, AW ;

Srivastava, M ;

Zhang, XM .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1969-1971

← 1 2 3 4 5 →