Influence of Bases and Ligands on the Outcome of the Cu(I)-Catalyzed Oxidative Homocoupling of Terminal Alkynes to 1,4-Disubstituted 1,3-Diynes Using Oxygen as an Oxidant

被引：133

作者：

Adimurthy, Subbarayappa ^{[2
]}

Malakar, Chandi C. ^{[1
]}

Beifuss, Uwe ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany

[2] Cent Salt & Marine Chem Res Inst, Bhavnagar 364002, Gujarat, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

关键词：

COUPLING REACTION; ROUTE;

D O I：

10.1021/jo900246z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient Cu(I)-catalyzed oxidative homocoupling; of terminal alkynes in the presence of a base using an amine as a ligand and oxygen as an oxidant yields the symmetrical 1,3-diynes with yields of up to 99%. The outcome of the couplings critically depends on the proper choice of base and ligand as well as reaction conditions. Best results were observed with 2.0 mol% CuCl, 1.5 mol% TMEDA or DBEDA, and DBU or DABCO in acetonitrile.

引用

页码：5648 / 5651

页数：4

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]

Bohlmann F., 1973, NATURALLY OCCURING A

[3]

Brandsma L, 1988, PREPARATIVE ACETYLEN

[4]

Cadiot P., 1969, CHEM ACETYLENES, P597

[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] OXIDATIVE COUPLING OF ACETYLENES [J].

HAY, AS .

JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (07) :1275-1276

[10] 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

← 1 2 3 →