Nickel-catalyzed oxidative coupling reactions of two different terminal alkynes using O(2) as the oxidant at room temperature: facile syntheses of unsymmetric 1,3-diynes

Org Lett. 2009 Feb 5;11(3):709-12. doi: 10.1021/ol8027863.

Abstract

Two different terminal alkynes now can be coupled together in the presence of NiCl(2).6H(2)O/CuI by using an excess of one of the terminal alkyne substrates. The new method employed 20 mol % TMEDA as the ligand and environmentally benign O(2) or air as the oxidant. It is the first example using Ni-salt as catalyst by employing air or O(2) as oxidant, which led to efficient heterocoupling of two different alkynes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry
  • Diynes / chemical synthesis*
  • Diynes / chemistry
  • Molecular Structure
  • Nickel / chemistry*
  • Oxidation-Reduction

Substances

  • Alkynes
  • Diynes
  • Copper
  • Nickel