1: CuBr2 / Ambient temperature 2: LAH / diethyl ether / 1) 0 deg C to room temperature, 2) reflux, overnight 3: Et3N / CH2Cl2 / 1) 0 deg C to room temperature, 2) room temperature, overnight 4: NaI / acetone / 48 h / Heating 5: Ph3SnH, AIBN / benzene / 80 °C View Scheme

1: CuBr2 / Ambient temperature 2: LAH / diethyl ether / 1) 0 deg C to room temperature, 2) reflux, overnight 3: Et3N / CH2Cl2 / 1) 0 deg C to room temperature, 2) room temperature, overnight 4: NaI / acetone / 48 h / Heating 5: Ph3SnH, AIBN / benzene / 80 °C View Scheme

1: Et3N / CH2Cl2 / 1) 0 deg C to room temperature, 2) room temperature, overnight 2: NaI / acetone / 48 h / Heating 3: Ph3SnH, AIBN / benzene / 80 °C View Scheme

1: LAH / diethyl ether / 1) 0 deg C to room temperature, 2) reflux, overnight 2: Et3N / CH2Cl2 / 1) 0 deg C to room temperature, 2) room temperature, overnight 3: NaI / acetone / 48 h / Heating 4: Ph3SnH, AIBN / benzene / 80 °C View Scheme

F-Oct3SnH; 2,2'-azo-bisisobutyronitrile; sodium cyanoborohydride in tert-butyl alcohol T=80°C; Yield givenYields of byproduct given;

(i) Li, (ii) /BRN= 509985/, (iii) liq. NH3; Multistep reaction;