The copper(I) thiophenolato complexes 1-3 containing 1,10-phenanthroline (phen) and 2,9-dimethyl-1,10-phenanthroline (Me(2)phen) were isolated in excellent yields from reactions of [CuOtBu](4) with the dative ligands and subsequent addition of 1 equiv of arylthiol and characterized spectroscopically. X-ray structural analysis of a single crystal of [(phen)Cu(µ-SC(6)H(5))](2) (1) revealed that this complex adopts a neutral dimeric form with a weak Cu-Cu bonding interaction. These complexes were found to react with iodoarenes to form aryl sulfide products. The intermediacy of such complexes in copper-catalyzed thioetherification of aryl halides was demonstrated by the reactivity with p-tolyl iodide and o-tolyl iodide to form two aryl thioethers with selectivities similar to those of catalytic reactions conducted with the same two iodoarenes.
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