1: With N-chloro-succinimide; diethylamine in dichloromethane Inert atmosphereCooling with ice; 2: With 2-pentafluorophenyl-6,17dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; water; triethylamine in dichloromethane T=20°C; 7 h; Inert atmosphere; chemoselective reaction;

phosgene; dimethyl sulfoxide; triethylamine in dichloromethane T=-78 - 0°C;

tetrabutyl-ammonium chloride; palladium diacetate; sodium hydrogencarbonate in N,N-dimethyl-formamide T=50°C; Heck Reaction; 6.5 h; Schlenk techniqueInert atmosphere;

oxygen; palladium diacetate; copper(l) chloride in dimethyl sulfoxide T=50°C; P=760.051 Torr; 20 h; regioselective reaction;

imidazolium dichromate in N,N-dimethyl-formamide 4 h; Ambient temperature;

1.1: Pd(OAc)2; NaOAc / 1-methyl-pyrrolidin-2-one / 120 °C 1.2: 1-methyl-pyrrolidin-2-one / 2 h / 135 °C 2.1: LiAlH4 / tetrahydrofuran / 1 h / 20 °C 2.2: 0.73 g / H2 / Pt/C / ethanol / 3 h / 20 °C / 760.05 Torr 3.1: 66 percent / (COCl2); DMSO; Et3N / CH2Cl2 / -78 - 0 °C View Scheme

1.1: LiAlH4 / tetrahydrofuran / 1 h / 20 °C 1.2: 0.73 g / H2 / Pt/C / ethanol / 3 h / 20 °C / 760.05 Torr 2.1: 66 percent / (COCl2); DMSO; Et3N / CH2Cl2 / -78 - 0 °C View Scheme

bis(cyclopentadienyl)titanium dichloride; triethyl amine hydrochloride; zinc in dichloromethane Inert atmosphere; chemoselective reaction;