sodium tetrahydroborate in methanol T=0°C; 0.166667 h;

sodium tetrahydroborate in methanol T=0°C; 0.0833333 h;

water T=40°C; 0.5 h;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride in ethanol; water; toluene T=80°C; Suzuki coupling; 1.5 h;

1: 70 percent / CeCl3*7H2O; NaBH4 / methanol / 12 h / 0 - 20 °C 2: Na2CO3; LiCl; Pd(Ph3P)4 / toluene; ethanol; H2O / 1.5 h / 80 °C View Scheme

1: 1.) CuI / 1.) ether, cyclohexane, -70 deg C, 2.) ether, cyclohexane, 0 deg C, 2 h 2: 1.) L-Selectride, 2.) n-Bu4NF / 1.) THF, -78 deg C. 30 min, 2.) THF, RT, 3 h 3: 26 percent / Ph3P, CBr4 / CH2Cl2 / 15 h / Ambient temperature 4: 8 percent / H2O2, CF3COOAg / diethyl ether / 0.5 h / 0 °C 5: 69 percent / NaBH4 / methanol / 0.08 h / 0 °C View Scheme

1: 83 percent / p-TsOH / dimethylformamide / 15 h / Ambient temperature 2: 1.) CuI / 1.) ether, cyclohexane, -70 deg C, 2.) ether, cyclohexane, 0 deg C, 2 h 3: 1.) L-Selectride, 2.) n-Bu4NF / 1.) THF, -78 deg C. 30 min, 2.) THF, RT, 3 h 4: 26 percent / Ph3P, CBr4 / CH2Cl2 / 15 h / Ambient temperature 5: 8 percent / H2O2, CF3COOAg / diethyl ether / 0.5 h / 0 °C 6: 69 percent / NaBH4 / methanol / 0.08 h / 0 °C View Scheme

1: 1.) L-Selectride, 2.) n-Bu4NF / 1.) THF, -78 deg C. 30 min, 2.) THF, RT, 3 h 2: 26 percent / Ph3P, CBr4 / CH2Cl2 / 15 h / Ambient temperature 3: 8 percent / H2O2, CF3COOAg / diethyl ether / 0.5 h / 0 °C 4: 69 percent / NaBH4 / methanol / 0.08 h / 0 °C View Scheme

1: 1.) CuI / 1.) ether, cyclohexane, -70 deg C, 2.) ether, cyclohexane, 0 deg C, 2 h 2: 1.) L-Selectride, 2.) n-Bu4NF / 1.) THF, -78 deg C. 30 min, 2.) THF, RT, 3 h 3: 26 percent / Ph3P, CBr4 / CH2Cl2 / 15 h / Ambient temperature 4: 8 percent / H2O2, CF3COOAg / diethyl ether / 0.5 h / 0 °C 5: 69 percent / NaBH4 / methanol / 0.08 h / 0 °C View Scheme

1: 26 percent / Ph3P, CBr4 / CH2Cl2 / 15 h / Ambient temperature 2: 8 percent / H2O2, CF3COOAg / diethyl ether / 0.5 h / 0 °C 3: 69 percent / NaBH4 / methanol / 0.08 h / 0 °C View Scheme