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

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 a...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 74; no. 15; pp. 5648 - 5651
Main Authors Adimurthy, Subbarayappa, Malakar, Chandi C, Beifuss, Uwe
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 07.08.2009
Subjects
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
1,8-Diazabicyclo[5.4.0]undec-7-ene
Catalytic reaction
Acetylenic compound
Nitrogen heterocycle
Ligand
Chemical base
Copper complex
Copper I Chlorides
Oxidant
Chemical coupling
Amine
Acetonitrile
Copper I
Oxidation
Homocoupling
Diynic compound
Alkyne
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo900246z