1: 1) n-BuLi / 1) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 15 min, 2) THF, 0 deg C to r.t. over 1 h then 2 h 2: 1) NaH / 1) THF, a) r.t., 2 h, b) 50 deg C, 1 h, 2) r.t., 6 h 3: benzene / 6 h / Heating 4: AIBN, (n-Bu)3SnH / benzene / 10 h / Heating View Scheme

1: 1) n-BuLi / 1) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 15 min, 2) THF, 0 deg C to r.t. over 1 h then 2 h 2: 1) NaH / 1) THF, a) r.t., 2 h, b) 50 deg C, 1 h, 2) r.t., 6 h 3: benzene / 6 h / Heating 4: AIBN, (n-Bu)3SnH / benzene / 10 h / Heating View Scheme

1: 1) NaH / 1) THF, a) r.t., 2 h, b) 50 deg C, 1 h, 2) r.t., 6 h 2: benzene / 6 h / Heating 3: AIBN, (n-Bu)3SnH / benzene / 10 h / Heating View Scheme

trimethylsilyl trifluoromethanesulfonate; trans-(PCy2Ph)2Ni(o-tolyl)Cl; triethylamine in dichloromethane T=20°C; Heck Reaction; 8 h; Overall yield = 70 percent; Overall yield = 140 mg; regioselective reaction;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 10 h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 2.) HCl / 1.) ether, 2 h, -20 to 0 deg C, 2.) -20 deg C to room temp. 2: 1.) MgBr2, 2.) Li / 1.) Et2O, 2.) THF View Scheme

lithium; magnesium bromide 1.) Et2O, 2.) THF; Yield given. Multistep reaction;

1: (S)-3-vinylcyclohexane With bis(1,5-cyclooctadiene)nickel (0); triethylamine; phenyldicyclohexylphosphine T=20°C; Heck type reaction; 0.0833333 h; Inert atmosphereSealed tubeneat (no solvent); 2: benzyl chloride With triethylsilyl trifluoromethanesulphonate T=20°C; Heck type reaction; 16 h; Inert atmosphereSealed tubeneat (no solvent);