Importance of bases on the copper-catalyzed oxidative homocoupling of terminal alkynes to 1,4-disubstituted 1,3-diynes

Copper-catalyzed, solvent-free oxidative homocoupling of terminal alkynes can be performed to 1,3-diynes in good to excellent yields in the absence of any additives, using air as environmentally friendly oxidant and the occurrence of water as an exclusive byproduct in the whole process. It is shown that AcO- of copper (II) acetate catalyst may take the role of base and found that the homocoupling cannot occur using weakly basic copper salt catalysts such as CuBr, CuCl, or Cul. Thus, the bases are absolutely necessary in the process of the homocoupling of terminal alkynes. (C) 2012 Elsevier Ltd. All rights reserved.