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
- Publikations-Art
- Zeitschriftenbeitrag (peer-reviewed)
- Autoren
- Adimurthy, S.; Malakar, C.C.; Beifuss, U.
- Erscheinungsjahr
- 2009
- Veröffentlicht in
- J. Org. Chem.
- Herausgeber
- American Chemical Society
- Band/Volume
- 74/15
- DOI
- 10.1021/jo900246z
- Seite (von - bis)
- 5648-5651
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.