1.1: LiOH / H2O; tetrahydrofuran / 0.33 h / 5 °C 2.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C 2.2: 5.5 mg / DMAP / toluene / 14 h / Heating 3.1: 85 percent / NaBH4 / methanol / 0.5 h / -78 °C 4.1: 95 percent / BF3*Et2O; thiophenol / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: 85 percent / p-chlorophenyl isocyanate; Et3N / benzene / 10 h / Heating 2.1: Mo(CO)6 / H2O; acetonitrile / 1.5 h / Heating 3.1: 35 mg / MsCl; Et3N / CH2Cl2 / 2 h / 20 °C 4.1: 97 percent / PPTS / ethanol / 10 h / 50 °C 5.1: LiOH / H2O; tetrahydrofuran / 0.33 h / 5 °C 6.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C 6.2: 5.5 mg / DMAP / toluene / 14 h / Heating 7.1: 85 percent / NaBH4 / methanol / 0.5 h / -78 °C 8.1: 95 percent / BF3*Et2O; thiophenol / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: 92 percent / LHMDS / tetrahydrofuran / 0.83 h / 0 °C 2.1: 95 percent / Li / tetrahydrofuran; ethanol; liquid ammonia / 0.5 h / -78 °C 3.1: 86 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 4.1: 98 percent / NaI / butan-2-one / 1.5 h / Heating 5.1: 75 percent / urea; NaNO2 / dimethylsulfoxide / 15 h / 20 °C 6.1: 95 percent / imidazole / dimethylformamide / 5 h / 20 °C 7.1: 85 percent / p-chlorophenyl isocyanate; Et3N / benzene / 10 h / Heating 8.1: Mo(CO)6 / H2O; acetonitrile / 1.5 h / Heating 9.1: 35 mg / MsCl; Et3N / CH2Cl2 / 2 h / 20 °C 10.1: 97 percent / PPTS / ethanol / 10 h / 50 °C 11.1: LiOH / H2O; tetrahydrofuran / 0.33 h / 5 °C 12.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C 12.2: 5.5 mg / DMAP / toluene / 14 h / Heating 13.1: 85 percent / NaBH4 / methanol / 0.5 h / -78 °C 14.1: 95 percent / BF3*Et2O; thiophenol / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: 85 percent / I2; Ph3P; imidazole / diethyl ether; acetonitrile / 0.5 h / 20 °C 2.1: 92 percent / LHMDS / tetrahydrofuran / 0.83 h / 0 °C 3.1: 95 percent / Li / tetrahydrofuran; ethanol; liquid ammonia / 0.5 h / -78 °C 4.1: 86 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 5.1: 98 percent / NaI / butan-2-one / 1.5 h / Heating 6.1: 75 percent / urea; NaNO2 / dimethylsulfoxide / 15 h / 20 °C 7.1: 95 percent / imidazole / dimethylformamide / 5 h / 20 °C 8.1: 85 percent / p-chlorophenyl isocyanate; Et3N / benzene / 10 h / Heating 9.1: Mo(CO)6 / H2O; acetonitrile / 1.5 h / Heating 10.1: 35 mg / MsCl; Et3N / CH2Cl2 / 2 h / 20 °C 11.1: 97 percent / PPTS / ethanol / 10 h / 50 °C 12.1: LiOH / H2O; tetrahydrofuran / 0.33 h / 5 °C 13.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C 13.2: 5.5 mg / DMAP / toluene / 14 h / Heating 14.1: 85 percent / NaBH4 / methanol / 0.5 h / -78 °C 15.1: 95 percent / BF3*Et2O; thiophenol / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: 97 percent / NaBH4 / ethanol / 8 h / 20 °C 2.1: 85 percent / I2; Ph3P; imidazole / diethyl ether; acetonitrile / 0.5 h / 20 °C 3.1: 92 percent / LHMDS / tetrahydrofuran / 0.83 h / 0 °C 4.1: 95 percent / Li / tetrahydrofuran; ethanol; liquid ammonia / 0.5 h / -78 °C 5.1: 86 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 6.1: 98 percent / NaI / butan-2-one / 1.5 h / Heating 7.1: 75 percent / urea; NaNO2 / dimethylsulfoxide / 15 h / 20 °C 8.1: 95 percent / imidazole / dimethylformamide / 5 h / 20 °C 9.1: 85 percent / p-chlorophenyl isocyanate; Et3N / benzene / 10 h / Heating 10.1: Mo(CO)6 / H2O; acetonitrile / 1.5 h / Heating 11.1: 35 mg / MsCl; Et3N / CH2Cl2 / 2 h / 20 °C 12.1: 97 percent / PPTS / ethanol / 10 h / 50 °C 13.1: LiOH / H2O; tetrahydrofuran / 0.33 h / 5 °C 14.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C 14.2: 5.5 mg / DMAP / toluene / 14 h / Heating 15.1: 85 percent / NaBH4 / methanol / 0.5 h / -78 °C 16.1: 95 percent / BF3*Et2O; thiophenol / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: 97 percent / PPTS / ethanol / 10 h / 50 °C 2.1: LiOH / H2O; tetrahydrofuran / 0.33 h / 5 °C 3.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C 3.2: 5.5 mg / DMAP / toluene / 14 h / Heating 4.1: 85 percent / NaBH4 / methanol / 0.5 h / -78 °C 5.1: 95 percent / BF3*Et2O; thiophenol / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: Mo(CO)6 / H2O; acetonitrile / 1.5 h / Heating 2.1: 35 mg / MsCl; Et3N / CH2Cl2 / 2 h / 20 °C 3.1: 97 percent / PPTS / ethanol / 10 h / 50 °C 4.1: LiOH / H2O; tetrahydrofuran / 0.33 h / 5 °C 5.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C 5.2: 5.5 mg / DMAP / toluene / 14 h / Heating 6.1: 85 percent / NaBH4 / methanol / 0.5 h / -78 °C 7.1: 95 percent / BF3*Et2O; thiophenol / CH2Cl2 / 0.5 h / 20 °C View Scheme

1: 95 percent / CBr4, PPh3 / dimethylformamide / 0 °C 2: 77 percent / acetonitrile / Heating 3: 1.) n-BuLi, LiBr, KOCMe3, 2.) HCl, 3.) LiOH / 1.) THF, -78 deg C, 2.) THF, room temperature, 10 h, 3.) MeOH, H2O, 10 h 4: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, 2.) TiCl4 / 1.) THF, toluene, reflux, 6 h, 2.) CH2Cl2, 0 deg C, 2 h View Scheme

1: 77 percent / acetonitrile / Heating 2: 1.) n-BuLi, LiBr, KOCMe3, 2.) HCl, 3.) LiOH / 1.) THF, -78 deg C, 2.) THF, room temperature, 10 h, 3.) MeOH, H2O, 10 h 3: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, 2.) TiCl4 / 1.) THF, toluene, reflux, 6 h, 2.) CH2Cl2, 0 deg C, 2 h View Scheme

1: 94 percent / NaBH4 / methanol / 0 °C 2: 95 percent / CBr4, PPh3 / dimethylformamide / 0 °C 3: 77 percent / acetonitrile / Heating 4: 1.) n-BuLi, LiBr, KOCMe3, 2.) HCl, 3.) LiOH / 1.) THF, -78 deg C, 2.) THF, room temperature, 10 h, 3.) MeOH, H2O, 10 h 5: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, 2.) TiCl4 / 1.) THF, toluene, reflux, 6 h, 2.) CH2Cl2, 0 deg C, 2 h View Scheme