1: H2 / Pd/C / tetrahydrofuran 2: 1.) (COCl)2 4: 96 percent / tris(2-methylphenyl)phosphine, Pd(OAc)2, Ag2CO3 / dimethylformamide / 3 h / Heating View Scheme

1: 89 percent / H2 / 20 percent Pd/C / ethanol / 760 Torr / Ambient temperature 2: 2.08 g / NEt3 / CH2Cl2 / 1 h / Ambient temperature 3: 96.4 percent / NaH / dimethylformamide / 0.5 h / Ambient temperature 4: 89 percent / tris(2-methylphenyl)phosphine, silver carbonate / Pd(OAc)2 / dimethylformamide / 2 h / Heating View Scheme