1.1: 95 percent / Et3N; DMAP / CH2Cl2 / 0.17 h / 20 °C 2.1: 80 percent / Cs2CO3; nBu4NI / acetonitrile / 1.5 h / 60 °C 3.1: 98 percent / Et3N; DMAP / CH2Cl2 / 1 h / 20 °C 4.1: 97 percent / Cs2CO3; thiophenol / acetonitrile / 10 h / 20 °C 5.1: 93 percent / ethanol / 24 h / 60 °C 6.1: 98 percent / ammonium fluoride / acetonitrile / 10 h / 60 °C 7.1: 90 percent / Ph3P; DEAD / CH2Cl2; benzene; toluene / 0.17 h / 20 °C 8.1: m-CPBA / CH2Cl2 / 1 h / -10 °C 8.2: 90 percent / Me2S / CH2Cl2 / -10 - 20 °C 9.1: 95 percent / SOCl2 / CH2Cl2; methanol / 2.5 h / 20 °C 10.1: 4(chlorodiphenylmethyl)phenoxymethylated polystyrene polymer; iPr2NEt / CH2Cl2 / 24 h / 20 °C 10.2: 2-mercaptoethanol; DBU / dimethylformamide / 26 h / 20 °C 10.3: TFA / CH2Cl2 / 0.08 h / 20 °C View Scheme

1: triethylamine / dimethylformamide / 24 h 2: 29.5 percent / NaBH4, tributyltin chloride / methanol / Irradiation 3: 96.2 percent / NaBH4, boron trifluoride etherate / tetrahydrofuran / 2 h / Ambient temperature View Scheme