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J Org Chem. 2009 Aug 7;74(15):5648-51. doi: 10.1021/jo900246z.

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.

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  • 1Central Salt & Marine Chemicals Research Institute, Gijubhai Badheka Marg, Bhavnagar 364 002, Gujrat, India.

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 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.

PMID:
19518122
DOI:
10.1021/jo900246z
[PubMed]
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