CuI/iodine-mediated homocoupling reaction of terminal alkynes to 1,3-diynes

被引：75

作者：

Li, Dafeng ^{[1
]}

Yin, Kun ^{[1
]}

Li, Jian ^{[1
]}

Jia, Xueshun ^{[1
]}

机构：

[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 41期

基金：

中国国家自然科学基金;

关键词：

CuI/iodine; homocoupling; terminal alkyne; 1,3-diyne;

D O I：

10.1016/j.tetlet.2008.07.138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient pathway for CuI/iodine-mediated homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted 1,3-diynes in good to excellent yields was reported. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5918 / 5919

页数：2

共 27 条

[1] Requirement for an oxidant in Pd/Cu co-catalyzed terminal alkyne homocoupling give symmetrical 1,4-disubstituted 1,3-diynes [J].

Batsanov, AS ;

Collings, JC ;

Fairlamb, IJS ;

Holland, JP ;

Howard, JAK ;

Lin, ZY ;

Marder, TB ;

Parsons, AC ;

Ward, RM ;

Zhu, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :703-706

[2]

Breitenbach J., 1996, COMPREHENSIVE SUPRAM, V2, P29

[3]

Cadiot P., 1969, Chemistry of Acetylenes, P597

[4] COMPLETELY SPIROCYCLOPROPANATED MACROCYCLIC OLIGODIACETYLENES - THE FAMILY OF EXPLODING [N]ROTANES [J].

DEMEIJERE, A ;

KOZHUSHKOV, S ;

HAUMANN, T ;

BOESE, R ;

PULS, C ;

COONEY, MJ ;

SCOTT, LT .

CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (02) :124-131

[5] MACROCYCLIC ACETYLENIC COMPOUNDS .1. CYCLOTETRADECA-1,3-DIYNE AND RELATED COMPOUNDS [J].

EGLINTON, G ;

GALBRAITH, AR .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAR) :889-896

[6] Pd-catalysed cross coupling of terminal alkynes to diynes in the absence of a stoichiometric additive [J].

Fairlamb, IJS ;

Bäuerlein, PS ;

Marrison, LR ;

Dickinson, JM .

CHEMICAL COMMUNICATIONS, 2003, (05) :632-633

[7]

Glaser C., 1869, Chem. Ber, V2, P422, DOI DOI 10.1002/CBER.186900201183

[8] OXIDATIVE COUPLING OF ACETYLENES .2. [J].

HAY, AS .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (09) :3320-&

[9] SYNTHESIS OF DICATIONIC DIARYLPYRIDINES AS NUCLEIC-ACID BINDING-AGENTS [J].

KUMAR, A ;

RHODE, RA ;

SPYCHALA, J ;

WILSON, WD ;

BOYKIN, DW ;

TIDWELL, RR ;

DYKSTRA, CC ;

HALL, JE ;

JONES, SK ;

SCHINAZI, RF .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (02) :99-106

[10] 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

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