Ligand-Free Synthesis of 1,4-Disubstituted-1,3-diynes by Iron/Copper Cocatalyzed Homocoupling of Terminal Alkynes

被引：15

作者：

Wang, Peipei ^{[1
]}

Liu, Xiaoyan ^{[1
]}

Zhang, Songlin ^{[1
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Jiangsu, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2013年 / 31卷 / 02期

基金：

中国国家自然科学基金;

关键词：

catalysis; copper; iron; 1; 3-diyne; ligand-free; CATALYZED DIRECT ARYLATION; COUPLING REACTION; N-ARYLATION; IRON; EFFICIENT; DIMERIZATION; PANAXYTRIOL; CHLORIDE; SYSTEM; ARENES;

D O I：

10.1002/cjoc.201200878

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and efficient protocol for Fe/Cu cocatalyzed oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted-1,3-diynes was presented. The results showed that both CuBr and FeCl3 played crucial roles in the reaction. It is noteworthy that this protocol employs mild, efficient, aerobic and ligand free conditions. The alkynes, including aromatic, heteroaromatic and aliphatic alkynes, were transformed into the corresponding 1,3-diynes in good to excellent yields.

引用

收藏

页码：187 / 194

页数：8

相关论文

共 77 条

[41] Ligand-Free Iron/Copper Cocatalyzed Alkynylation Coupling Reactions [J].

Mao, Jincheng ;

Xie, Guanlei ;

Wu, Minyan ;

Guo, Jun ;

Ji, Shunjun .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (16) :2477-2482

[42] SYNTHESIS OF 1-PHENYL-2,5-DIARYL (DIALKYL)-ARSOLES - REACTION OF ARSOLES WITH ALKALI-METALS AND ORGANO-LITHIUM COMPOUNDS [J].

MARKL, G ;

HAUPTMANN, H ;

MERZ, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 249 (02) :335-363

[43]

Martin RE, 1999, ANGEW CHEM INT EDIT, V38, P1350, DOI 10.1002/(SICI)1521-3773(19990517)38:10<1350::AID-ANIE1350>3.0.CO

[44]

2-6

[45] Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-panaxytriol and (R)- and (S)-falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction [J].

Mayer, SF ;

Steinreiber, A ;

Orru, RVA ;

Faber, K .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9115-9121

[46]

Meijere A.D., 1995, CHEM-EUR J, V1, P124

[47] Iron/copper promoted oxidative homo-coupling reaction of terminal alkynes using air as the oxidant [J].

Meng, Xu ;

Li, Chuanbin ;

Han, Baochun ;

Wang, Tiansheng ;

Chen, Baohua .

TETRAHEDRON, 2010, 66 (23) :4029-4031

[48] A Simple One-Pot Procedure for the Direct Homocoupling of Terminal Alkynes Promoted by Copper Nanoparticles [J].

Nador, Fabiana ;

Fortunato, Leandro ;

Moglie, Yanina ;

Vitale, Cristian ;

Radivoy, Gabriel .

SYNTHESIS-STUTTGART, 2009, (23) :4027-4031

[49] Effect of TMEDA on Iron-Catalyzed Coupling Reactions of ArMgX with Alkyl Halides [J].

Noda, Daisuke ;

Sunada, Yusuke ;

Hatakeyama, Takuji ;

Nakamura, Masaharu ;

Nagashima, Hideo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6078-+

[50] Heterogeneously Catalyzed Efficient Alkyne-Alkyne Homocoupling by Supported Copper Hydroxide on Titanium Oxide [J].

Oishi, Takamichi ;

Katayama, Tatsuyori ;

Yamaguchi, Kazuya ;

Mizuno, Noritaka .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (31) :7539-7542

← 1 2 3 4 5 6 7 8 →