sodium tetrahydroborate in methanol T=-78°C;

K(iPrO)3BH The ratio of these reduced products was also studied starting from 3-tributylstannylpyridine by a multistep procedure.; Product distribution;

1: 1.) POCl3, 2.) KOAc / 1.) CH2Cl2, RT, 20 h, 2.) CH2Cl2, water, reflux, 20 min 2: 54 percent / sulfur / various solvent(s) / 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