trifluoromethylsulfonic anhydride; diphenyltin sulfide; cesium fluoride in diethyl ether

trimethylsilyl bromide; tetrabutylammomium bromide; cobalt(II) dibromide; 4 A molecular sieve in dichloromethane T=25°C;

sodium hydride in methanol 30 h;

{1,2-benzenediolato(2-)-O,O'}oxotitanium; trifluoromethanesulfonic acid anhydride; N-ethyl-N,N-diisopropylamine; cesium fluoride Yield given. Multistep reaction. Yields of byproduct given;

4-(N,N-dimethlyamino)pyridine T=20°C; 3 h;

pyridine

triethylamine

1.1: 82 percent / 0.5 h / 110 °C 2.1: n-BuLi / hexane; diethyl ether / -78 - -70 °C 2.2: 55 percent / tetrahydrofuran; diethyl ether; hexane / 5 h / -70 °C 3.1: (AcO)2Cu*H2O; Zn / acetic acid; H2O / 0.75 h / 20 - 70 °C 4.1: 71 percent / 4 Angstroem molecular sieves; pyridine; Tf2O / 0.5 h / 40 °C 5.1: 4 Angstroem molecular sieves; methyl triflate / acetonitrile / 0.5 h 5.2: NaBH4 / methanol / 0.17 h / 20 °C 5.3: AgNO3 / acetonitrile; H2O / 0.17 h / 20 °C 6.1: 0.39 g / NaBH4 / acetonitrile; H2O / 0 - 20 °C 7.1: 78 percent / H2 / Pd(OH)2 / acetic acid / 12 h / atmospheric pressure View Scheme

sodium tetrahydroborate in ethanol T=50°C; 1 h;

1: HCl, MgSO4 / 1 h / 0 °C 2: pyridine / Ambient temperature View Scheme