Yield given. Multistep reaction;

1: acetonitrile / 20 °C 2: triethylamine / 0 °C 3: 1,10-phenanthroline; potassium hexacyano-ferrate / acetonitrile / 12 h / 70 °C / |Schlenk technique; |Inert atmosphere View Scheme

1.1: tetrabutylammonium chloride; triethylamine / [(C5Me5)Ru(NCCH3)3]PF6 / 35 °C 2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 35 °C 2.2: 99 percent / KOH; H2O2 / 0 °C 3.1: (C2H5)3N / CH2Cl2 / 0 °C 4.1: methanol / 70 °C View Scheme

hydrogen; palladium on activated charcoal in methanol T=20°C;

hydrogen; nickel 1.5 h;

Hydrogenation;

1: 67 percent / pyridine / CH2Cl2 / 18 h / Heating 2: <W(CO)3(η6-C7H8)>, 2-2'-bipyridine / tetrahydrofuran / 18 h / 60 °C View Scheme

1: 67 percent / pyridine / CH2Cl2 / 18 h / Heating 2: 84 percent / <W(CO)3(η6-C7H8)>, 2-2'-bipyridine / tetrahydrofuran / 18 h / 60 °C View Scheme

1: (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; (S)-phenyl vinyl carbinol / 1,2-dichloro-ethane / 24 h / 23 - 50 °C / Inert atmosphere 2: (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; C11H11ClO2 / 1,2-dichloro-ethane / 24 h / 23 - 50 °C / Inert atmosphere View Scheme