Sn[N(SiMe3)2]2 in hexane 12 h; Ambient temperature;

1: 1.) boron trifluoride etherate / 1.) THF, 0 deg C; 0 deg C to RT, 70 min; 2.) THF, RT, 14 h 2: 1.) LAH; 2.) NaOH, water / tetrahydrofuran / 1.) 0 deg C to RT, 3.5 h; 2.) RT, 20 min 3: 91 percent / triphenylphosphine, imidazole, iodine / diethyl ether; acetonitrile / 14 h / Ambient temperature 4: 93 percent / dimethylsulfoxide / 2 h / 8 °C 5: 79 percent / n-butyllithium / tetrahydrofuran; hexane / 1.5 h / 0 °C 6: 84 percent / glacial acetic acid, triphenylphosphine / toluene / 48 h / Heating 7: 88 percent / SN<N(TMS)2>2 / hexane / 12 h / Ambient temperature View Scheme

1: 93 percent / dimethylsulfoxide / 2 h / 8 °C 2: 79 percent / n-butyllithium / tetrahydrofuran; hexane / 1.5 h / 0 °C 3: 84 percent / glacial acetic acid, triphenylphosphine / toluene / 48 h / Heating 4: 88 percent / SN<N(TMS)2>2 / hexane / 12 h / Ambient temperature View Scheme