ammonium formate; Pd(dibenzylidene acetone)3*CHCl3; tributylphosphine in 1,4-dioxane 2 h; Heating;

1: 91 percent / Li2CuCl4 / tetrahydrofuran / 1.) -5 deg C, 3 h, 20 deg C, 12 h 2: 1) 9-BBN, 2.) 26percent H2O2, 3 N NaOH / 1.) THF, 20 deg C, 2 h, 2.) 20 deg C, 2 h View Scheme

1: 84 percent / Li2CuCl4 / tetrahydrofuran; diethyl ether / 3 h / 0 °C 2: 1.) 0.75M 9-borabicyclo<3.3.1>nonane; 2.) 3N NaOH, 26percent H2O2 / 1.) THF, 0 deg C, 2-3 h; 2.) 20 deg C, 2-3 h 3: PBr3 / 1.) pyridine, hexane, 3-5 deg C, 3h; 2.) 20 deg C, 12 h 4: 1.) Mg / 1.) ether; 2.) ether; HCl 5: 90 percent / LiAlH4 / diethyl ether View Scheme

hydrogen; bis(acetylacetonato) palladium T=20°C; P=750.075 Torr; 24 h; Product distribution; Further Variations:CatalystsReagentsTemperatures;

dilithium tetrachlorocuprate in tetrahydrofuran