The use of toluene instead of THF minimizes unwanted diarylation (8c) with SIPr (entry 6), but poor conversion is observed with SIMes in toluene (entry 7). Dimethylformamide (DMF) is an effective solvent for the reaction with SIMes(entry 9) but not with SIPr (entry 8), while 1,4-dioxane is an effective solvent with both ligands (entries 10−11). Control reactions demonstrate that the catalyst, KF, and water are each necessary for both the triflate- and the chloride-selective cross-couplings using SIMes and SIPr, respectively (entries 8−13).Furthermore, only trace cross-coupling products are detected under ligand-free conditions using [(η3-1-tBu-indenyl)Pd-(Cl)]2(9, entry 14).