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

Publication Type
Journal contribution (peer reviewed)
Authors
Adimurthy, S.; Malakar, C.C.; Beifuss, U.
Year of publication
2009
Published in
J. Org. Chem.
Editor
American Chemical Society
Band/Volume
74/15
DOI
10.1021/jo900246z
Page (from - to)
5648-5651
Abstract

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 sym. 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 obsd. with 2.0 mol % CuCl, 1.5 mol % TMEDA or DBEDA, and DBU or DABCO in acetonitrile.

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