sodium tetrahydroborate; water; dihydridotetrakis(triphenylphosphine)ruthenium(II) in toluene T=100°C; 22 h;

lithium triethylborohydride in tetrahydrofuran T=0 - 20°C; 1 h;

[1,3-bis(diphenylphosphino) propane] dichloronickel(II); trimethylaluminum in hexane; toluene 7 h; Heating;

1.1: TMEDA; t-BuLi / tetrahydrofuran / 3 h / -78 °C 1.2: 50 percent / tetrahydrofuran / 12 h / -78 - 20 °C 2.1: 86 percent / P2O5 / CH2Cl2 / Heating 3.1: 52 percent / dichloro(benzylidene)bis(tricyclohexylphosphine)ruthenium / benzene / 60 °C View Scheme

water; oxygen; copper dichloride; palladium dichloride in tetrahydrofuran T=50°C; Yield given;