magnesium sulfate in diethyl ether T=20°C; 20 h;

[RuH2(η2-H2)2(PCy3)2] in toluene

1: in tetrahydrofuran T=-20°C; 1.5 h; Inert atmosphere; 2: With acetyl chloride in tetrahydrofuran Inert atmosphere;

in tetrahydrofuran; toluene T=-20 - 0°C; Inert atmosphere;

n-butyllithium in tetrahydrofuran; hexane byproducts: BuI; boronic ester and ICH2Cl in rigorously dried THF cooled to -78°Cand stirred under Ar during dropwise addn. of 1.6 M n-BuLi in hexane, kept overnight at 20-25°C; concd. in vac., treated with petroleum ether and concd. aq. NH4Cl, org.phase dried over MgSO4, distilled bulb to bulb in vac.;

1.1: Schwartz's reagent / tetrahydrofuran / 1 h / 20 °C / |Inert atmosphere 1.2: 1 h / 20 °C / |Inert atmosphere 2.1: hydrogen; [Ir((S)-PPh2C6H4C3H3NOiPr)(COD)](tetrakis(3,5-di(trifluoromethyl)phenyl)borate) / dichloromethane / 18 h / 50 °C / 22502.3 Torr View Scheme

1.1: Schwartz's reagent / tetrahydrofuran / 1 h / 20 °C / |Inert atmosphere 1.2: 1 h / 20 °C / |Inert atmosphere 2.1: hydrogen; (C5H2N(C6H5))CH2CH2CH(O)P(C(CH3)3)2Ir(C8H12)(1+)*B(C8H3F6)4(1-)=(C5H2N(C6H5))CH2CH2CH(O)P(C(CH3)3)2Ir(C8H12)B(C8H3F6)4 / dichloromethane / 18 h / 50 °C / 22502.3 Torr View Scheme