1: vinyl-magnesium bromide With boric acid trimethyl ester in tetrahydrofuran T=-78°C; 1 h; 2: With hydrogenchloride in tetrahydrofuran; diethyl ether T=20°C; 0.166667 h; 3: 1,1,3-trimethyl-1,3-propanediol in tetrahydrofuran; diethyl ether T=20°C; 1 h;

hydrogenchloride in tetrahydrofuran; diethyl ether under Ar; soln. CH2CHMgBr in THF added dropwise over 1 h to stirred soln. of anhyd. B(OMe)3 in THF at -78°C; stirred for 1 h; warmed to room temp.; 20percent HCl added; 10 min; soln. of diol in Et2O added; stirred for 1 h; two phases sepd.; aq. phase extd. with Et2O; combined org. extracts washed with satd. aq. NaHCO3 and water; dried (MgSO4); solvent evapd.; purified by Kugelroehr distn.;

hydrogen; Lindlar's catalyst in cyclohexane

1: (i) Et2O, (ii) (pyrolysis) 2: H2 / Pd-CaCO3 / cyclohexane View Scheme

Schwartz's reagent T=20°C;

in tetrahydrofuran; diethyl ether

tributyl-amine; triphenylphosphine; palladium diacetate in toluene Heck coupling; 96 h; Heating;

silver(l) oxide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=67°C; Suzuki-Miyaura reaction; 24 h;

potassium tert-butylate; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=67°C; Suzuki-Miyaura reaction; 24 h;

silver(l) oxide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=67°C; Suzuki-Miyaura reaction; 24 h;