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

页码：187 / 194

页数：8

共 77 条

[21] Efficient N-arylation of amines catalyzed by Cu-Fe-hydrotalcite [J].

Jadhav, Vinod H. ;

Dumbre, Deepa K. ;

Phapale, Vilas B. ;

Borate, Hanumant B. ;

Wakharkar, Radhika D. .

CATALYSIS COMMUNICATIONS, 2007, 8 (01) :65-68

[22] 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

[23] Factors determining the course and mechanisms of Grignard reactions. IV. The effect of metallic halides on the reaction of aryl Grignard reagents and organic halides [J].

Kharasch, MS ;

Fields, EK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :2316-2320

[24] The first synthesis of a diynone from Echinacea pallida [J].

Kraus, GA ;

Bae, J ;

Schuster, J .

SYNTHESIS-STUTTGART, 2005, (20) :3502-3504

[25] Organic reaction in Solkane® 365 mfc: homocoupling reaction of terminal alkynes [J].

Kusuda, Akihiro ;

Xu, Xiu-Hua ;

Wang, Xin ;

Tokunaga, Etsuko ;

Shibata, Norio .

GREEN CHEMISTRY, 2011, 13 (04) :843-846

[26] 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

[27] CuI/iodine-mediated homocoupling reaction of terminal alkynes to 1,3-diynes [J].

Li, Dafeng ;

Yin, Kun ;

Li, Jian ;

Jia, Xueshun .

TETRAHEDRON LETTERS, 2008, 49 (41) :5918-5919

[28] Efficient palladium-catalyzed homocoupling reaction and Sonogashira cross-coupling reaction of terminal alkynes under aerobic conditions [J].

Li, JH ;

Liang, Y ;

Xie, YX .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4393-4396

[29] Amine- and phosphine-free palladium(II)-catalyzed homocoupling reaction of terminal alkynes [J].

Li, JH ;

Yun, L ;

Zhang, XD .

TETRAHEDRON, 2005, 61 (07) :1903-1907

[30] A mild copper-mediated Glaser-type coupling reaction under the novel CuI/NBS/DIPEA promoting system [J].

Li, Lingjun ;

Wang, Jiuxia ;

Zhang, Guisheng ;

Liu, Qingfeng .

TETRAHEDRON LETTERS, 2009, 50 (28) :4033-4036

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