1: 75 percent / O2 gas / PdCl2, CuCl2 / dimethylformamide; H2O / 25 °C 2: 70 percent / BF3*Et2O / CH2Cl2 / 0 - 25 °C 3: 1.) NaH, 2.) 1N HCl / 1.) THF, reflux, 5 h, 2.) MeOH, 25 deg C 4: 60 percent / Raney Ni / ethanol View Scheme

With  oxygen; copper dichloride; palladium dichloride in  water; N,N-dimethyl-formamide T=25°C;   

Multi-step reaction with 2 steps 1: 75 percent / O2 gas / PdCl2, CuCl2 / dimethylformamide; H2O / 25 °C2: 70 percent / BF3*Et2O / CH2Cl2 / 0 - 25 °C  

Multi-step reaction with 3 steps 1: 75 percent / O2 gas / PdCl2, CuCl2 / dimethylformamide; H2O / 25 °C2: 70 percent / BF3*Et2O / CH2Cl2 / 0 - 25 °C3: 1.) NaH, 2.) 1N HCl / 1.) THF, reflux, 5 h, 2.) MeOH, 25 deg C