1: 94 percent / lithium hexamethyldisilazide / tetrahydrofuran / -78 °C 2: 27 percent / Grubbs catalyst 1st generation / benzene / Heating 3: 58 percent / CsF; Pd(PPh3)4 / 1,2-dichloro-ethane / 80 °C 4: 24 percent / Grubbs 2nd generation catalyst / benzene / Heating View Scheme

1: 27 percent / Grubbs catalyst 1st generation / benzene / Heating 2: 58 percent / CsF; Pd(PPh3)4 / 1,2-dichloro-ethane / 80 °C 3: 24 percent / Grubbs 2nd generation catalyst / benzene / Heating View Scheme

1: 58 percent / CsF; Pd(PPh3)4 / 1,2-dichloro-ethane / 80 °C 2: 24 percent / Grubbs 2nd generation catalyst / benzene / Heating View Scheme

1: 83 percent / tetrahydrofuran 2: 94 percent / lithium hexamethyldisilazide / tetrahydrofuran / -78 °C 3: 27 percent / Grubbs catalyst 1st generation / benzene / Heating 4: 58 percent / CsF; Pd(PPh3)4 / 1,2-dichloro-ethane / 80 °C 5: 24 percent / Grubbs 2nd generation catalyst / benzene / Heating View Scheme

formic acid; ascorbic acid powder in water T=100°C; 4 h;

Grubb's 2nd generation catalyst in benzene Heating;

hydrogenchloride 0.25 h; Yield given. Yields of byproduct given;