The oxidative addition, of o-(Me2RSiCH2O)C6H4I (R=Me, Ph, F) to palladium(0) complexes leads to the corresponding completes o-(Me2RCH2O)C6H4Pd(L-2)I (L=PPh3, AsPh3; L-2=dppf). The intramolecular Pd/Si transmetalation proceeds smoothly with fluorides and carbonates as the promoters.