sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in water; toluene 2.5 h; Heating / reflux;

sulfur in decalin 2 h; Heating;

1: 35 percent / NaBH4 / methanol / -78 °C 2: 67 percent / bis(1,3-diphenylphosphino)propanenickel(II) chloride / benzene; tetrahydrofuran / 2 h / Ambient temperature 3: 1.) POCl3, 2.) KOAc / 1.) CH2Cl2, RT, 4.5 h, 2.) CH2Cl2, water, reflux, 20 min 4: 51 percent / sulfur / decahydronaphthalene / 2 h / Heating View Scheme

1: 67 percent / bis(1,3-diphenylphosphino)propanenickel(II) chloride / benzene; tetrahydrofuran / 2 h / Ambient temperature 2: 1.) POCl3, 2.) KOAc / 1.) CH2Cl2, RT, 4.5 h, 2.) CH2Cl2, water, reflux, 20 min 3: 51 percent / sulfur / decahydronaphthalene / 2 h / Heating View Scheme

1: 1.) POCl3, 2.) KOAc / 1.) CH2Cl2, RT, 4.5 h, 2.) CH2Cl2, water, reflux, 20 min 2: 51 percent / sulfur / decahydronaphthalene / 2 h / Heating View Scheme

1: bromine; acetic acid / 2.5 h / Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; water; toluene / Inert atmosphere; Reflux View Scheme