triethylsilane; trifluoroacetic acid in dichloromethane T=20°C;

CsO2CCMe3; bis(1,1-diphenylphosphino)methane; palladium diacetate in N,N-dimethyl-formamide T=120°C; 2 h;

diisobutylaluminium hydride in diethyl ether; hexane T=-40°C; 0.5 h;

1: N-chlorosuccinimide, dimethyl sulfide, triethylamine / toluene / -20 °C 2: 95 percent / hydrochloric acid / aq. ethanol 3: 68 percent / sodium hydride / CH2Cl2 4: 53 percent / chlorobenzene / 0.5 h / Heating 5: 97 percent / lithium aluminum hydride / diethyl ether / 96 h / Ambient temperature View Scheme

N-chloro-succinimide; dimethylsulfide; triethylamine in toluene T=-20°C;