text: In coupling reactions between aromatic compounds and metal-trifluoromethyl complexes the metal is usually copper, Pd and Ni are less prominent. The reactions are stoichiometric or catalytic. In the McLoughlin-Thrower reaction (1962) iodobenzene reacts with trifluoroiodomethane (CFI) and copper powder  in dimethylformamide at 150 °C to trifluoromethylbenzene. The intermediate in this reaction type is a perfluoromethyl-metal complex.
  A palladium acetate catalysed reaction described in 1982 used zinc powder with the main intermediate believed to be CFZnI with Pd(0) is the active catalyst. The first copper catalysed coupling was reported in 2009 and based on an iodoarene, a trifluoromethylsilane, copper iodide and 1,10-phenanthroline. Variations include another CF donor potassium (trifluoromethyl)trimethoxyborate, the use of aryl boronic acids or the use of a trifluoromethyl sulfonium salt or the use of a trifluoromethylcopper(I) phenanthroline complex. A catalytic palladium catalysed reaction was reported in 2010 using aryl halides, (trifluoromethyl)triethylsilane and allylpalladium chloride dimer