boron tribromide in dichloromethane 24 h; Inert atmosphere;

trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether; trifluoroacetic acid 0.5 h; Ambient temperature;

1: 81 percent / BF3*Et2O / toluene / 4 h / Heating 3: 74 percent / N-bromosuccinimide (NBS), 2,6-lutidine, H2O / acetonitrile / 0.08 h / 0 °C 4: 99 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 1 h / Ambient temperature 5: 95 percent / NEt3/C / ethanol; CHCl3 / 48 h / Ambient temperature 6: 100 percent / LiOH, H2O / dioxane / 12 h / Ambient temperature 7: 100 percent / H2, <Rh<cycloocta-1,5-diene><(R,R)-1,2-bis<2-(2-methoxyphenyl)phenylphosphino>ethane>>+*BF4- / methanol / 72 h / Ambient temperature 8: 82 percent / dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP) / ethyl acetate / 12 h / -15 - 20 °C 9: 84 percent / pyridinium-p-toluene sulphonate, H2O / acetone / 6 h / Heating 10: 93 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 2 h / Ambient temperature 11: NEt3/C / ethanol; CHCl3 / 48 h / Ambient temperature 12: H2, <Rh<cycloocta-1,5-diene><(R,R)-1,2-bis<2-(2-methoxyphenyl)phenylphosphino>ethane>>+*BF4- / methanol / 72 h / Ambient temperature 13: 100 percent / 6 M HCl / dioxane / 2 h / 20 °C 14: 71 percent / N-(3-dimethylaminopropyl)-N'-ethylcarboimide hydrochloride (EDC), hydroxybenzotriazole / CH2Cl2 / 14 h / 15 - 20 °C 15: 85 percent / AcOH, H2O / 7 h / 50 °C 16: Bu4NF / dimethylformamide / 1 h / Ambient temperature 17: 95 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) / CH2Cl2 / 14 h / -15 - 20 °C 18: 1.) 6 M HCl, 2.) NaHCO3 / 1.) dioxane, CH2Cl2, 0 deg C, 2.) CHCl3, 20 deg C, 5 min 19: 70 percent / trimethylsilyl trifluoromethane sulphonate, thioanisole, CF3CO2H / 0.5 h / Ambient temperature View Scheme

2: 74 percent / N-bromosuccinimide (NBS), 2,6-lutidine, H2O / acetonitrile / 0.08 h / 0 °C 3: 99 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 1 h / Ambient temperature 4: 95 percent / NEt3/C / ethanol; CHCl3 / 48 h / Ambient temperature 5: 100 percent / LiOH, H2O / dioxane / 12 h / Ambient temperature 6: 100 percent / H2, <Rh<cycloocta-1,5-diene><(R,R)-1,2-bis<2-(2-methoxyphenyl)phenylphosphino>ethane>>+*BF4- / methanol / 72 h / Ambient temperature 7: 82 percent / dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP) / ethyl acetate / 12 h / -15 - 20 °C 8: 84 percent / pyridinium-p-toluene sulphonate, H2O / acetone / 6 h / Heating 9: 93 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 2 h / Ambient temperature 10: NEt3/C / ethanol; CHCl3 / 48 h / Ambient temperature 11: H2, <Rh<cycloocta-1,5-diene><(R,R)-1,2-bis<2-(2-methoxyphenyl)phenylphosphino>ethane>>+*BF4- / methanol / 72 h / Ambient temperature 12: 100 percent / 6 M HCl / dioxane / 2 h / 20 °C 13: 71 percent / N-(3-dimethylaminopropyl)-N'-ethylcarboimide hydrochloride (EDC), hydroxybenzotriazole / CH2Cl2 / 14 h / 15 - 20 °C 14: 85 percent / AcOH, H2O / 7 h / 50 °C 15: Bu4NF / dimethylformamide / 1 h / Ambient temperature 16: 95 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) / CH2Cl2 / 14 h / -15 - 20 °C 17: 1.) 6 M HCl, 2.) NaHCO3 / 1.) dioxane, CH2Cl2, 0 deg C, 2.) CHCl3, 20 deg C, 5 min 18: 70 percent / trimethylsilyl trifluoromethane sulphonate, thioanisole, CF3CO2H / 0.5 h / Ambient temperature View Scheme

1: 95 percent / NEt3/C / ethanol; CHCl3 / 48 h / Ambient temperature 2: 100 percent / LiOH, H2O / dioxane / 12 h / Ambient temperature 3: 100 percent / H2, <Rh<cycloocta-1,5-diene><(R,R)-1,2-bis<2-(2-methoxyphenyl)phenylphosphino>ethane>>+*BF4- / methanol / 72 h / Ambient temperature 4: 82 percent / dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP) / ethyl acetate / 12 h / -15 - 20 °C 5: 84 percent / pyridinium-p-toluene sulphonate, H2O / acetone / 6 h / Heating 6: 93 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 2 h / Ambient temperature 7: NEt3/C / ethanol; CHCl3 / 48 h / Ambient temperature 8: H2, <Rh<cycloocta-1,5-diene><(R,R)-1,2-bis<2-(2-methoxyphenyl)phenylphosphino>ethane>>+*BF4- / methanol / 72 h / Ambient temperature 9: 100 percent / 6 M HCl / dioxane / 2 h / 20 °C 10: 71 percent / N-(3-dimethylaminopropyl)-N'-ethylcarboimide hydrochloride (EDC), hydroxybenzotriazole / CH2Cl2 / 14 h / 15 - 20 °C 11: 85 percent / AcOH, H2O / 7 h / 50 °C 12: Bu4NF / dimethylformamide / 1 h / Ambient temperature 13: 95 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) / CH2Cl2 / 14 h / -15 - 20 °C 14: 1.) 6 M HCl, 2.) NaHCO3 / 1.) dioxane, CH2Cl2, 0 deg C, 2.) CHCl3, 20 deg C, 5 min 15: 70 percent / trimethylsilyl trifluoromethane sulphonate, thioanisole, CF3CO2H / 0.5 h / Ambient temperature View Scheme