1: diethyl ether 2: NaNH2; decalin / 150 °C View Scheme

1: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane With CuCl(C3H4N2(C10H15)2); sodium t-butanolate in tetrahydrofuran T=22°C; 0.5 h; Inert atmosphere; 2: 3-cyclopentyl-1-propyne With methanol in tetrahydrofuran T=22°C; 12 h; Inert atmosphere; regioselective reaction;

1: With [1,3-bis(diphenylphosphino) propane] dichloronickel(II); diisobutylaluminium hydride in tetrahydrofuran T=0 - 22°C; Inert atmosphere; 2: With water; Potassium sodium tartrate in tetrahydrofuran T=0°C; 0.5 h;

1: 92 percent / CuI, (PPh3)2PdCl2, Et3N / dioxane / 1 h / Ambient temperature 2: 300 mg / conc. NH4OH / dioxane / 20 h / 70 °C View Scheme

1: With 2,6-dimethylbenzeneamine; [(η5-cyclopentadienyl)2Ti(η2-Me3SiC2SiMe3)] in toluene T=85°C; 24 h; 2: With hydrogenchloride