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The screening reactions were performed with respect to the solvent, base, and palladium source (see Supporting Information for the details). The oxidative addition of ArCl to Pd(0) usually requires a bulky, electron-rich phosphine, a secondary phosphine oxide, or an N-heterocyclic carbene (NHC).Optimization revealed that neither phospine oxide nor NHC ligands are effective. Electron-rich, bulky butyldi-1-adamantylphosphine and tert -butyldicyclohexylphosphine afforded the best results, and the former was chosen because of cost considerations (Table 1). Among the bases screened,use of CsOAc, CsF, K3PO4,K2CO3, and Cs2CO3 resulted in reasonable conversions to the product. Potassium phosphate afforded somewhat better selectivity for monoarylation, is cheaper than the cesium salts, and was used in all subsequent reactions. Evaluation of palladium sources revealed that palladium acetate is superior to all other choices. Optimiza- tion with respect to solvent showed that the reaction proceeds best in NMP. The optimized conditions thus include NMP solvent, K3PO4 base, butyldi-1-adamantylphosphine ligand,and Pd(OAc)2 catalyst. |
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