Uses
Copper(I) phenylacetylide participates in efficient coupling with a range of aryl iodides and bromides to give substituted tolanes?which, if possessing an?ortho?amino or hydroxy group, can be thermolyzed to yield 2-phenylbenzofurans, -indoles, and -furo[3,2-b]pyridines.
Preparation
(i) Phenylacetylene is treated with either ammoniacal Copper(II) Sulfate and Hydroxylamine hydrochloride (reductant) or Copper(I) Iodide in ethanol; (ii) phenylacetylene is lithiated, then treated with copper(I) iodide; (iii) phenylacetylene is treated with Copper(I) t-Butoxide.
Drying: heat (65 °C) under vacuum.
Application
Copper (i) phenylacetylide is a mild nucleophile used to introduce phenylethynyl groups to form phenylpropene and Glazer cross-coupling products.
storage
All copper(I) acetylides are potentially explosive in the solid state. Use in a fume hood.
