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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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
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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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo900246z