sodium sulfide in methanol Heating;

Lawesson's reagent in toluene Heating;

1: 1.) triphenylphosphine (PPh3), Zn dust / 1.) CH2Cl2, RT, 38 h; 2.) CH2Cl2, a.) 0 deg C; b.) RT, 6 h 2: 1.) 2.3M methyllithium, 2.) H(1+) / 1.) ether, a.) -78 deg C, 1 h; b.) up to RT; c.) RT, 1 h; 2.) ether 3: 90 percent / Et3N, chloroacetone / CuI, tetrakis(triphenylphosphine) palladium(0) <(PPh3)4Pd> / benzene / Ambient temperature 4: 65 percent / Na2S*9H2O / methanol / Heating View Scheme

1: 90 percent / Et3N, chloroacetone / CuI, tetrakis(triphenylphosphine) palladium(0) <(PPh3)4Pd> / benzene / Ambient temperature 2: 65 percent / Na2S*9H2O / methanol / Heating View Scheme

1: 1.) 2.3M methyllithium, 2.) H(1+) / 1.) ether, a.) -78 deg C, 1 h; b.) up to RT; c.) RT, 1 h; 2.) ether 2: 90 percent / Et3N, chloroacetone / CuI, tetrakis(triphenylphosphine) palladium(0) <(PPh3)4Pd> / benzene / Ambient temperature 3: 65 percent / Na2S*9H2O / methanol / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran 72 h; Heating;

1: 1.68 g / aq. HCl / ethanol / 16 h / Heating 2: 65 percent / sodium cyanide / dimethylformamide 3: 70 percent / Lawesson's reagent / toluene / Heating View Scheme

1: 65 percent / sodium cyanide / dimethylformamide 2: 70 percent / Lawesson's reagent / toluene / Heating View Scheme