Grubb's 2nd generation catalyst in dichloromethane 6 h; Heating;

toluene-4-sulfonic acid; hydroquinone in toluene 0.5 h; Heating;

1: tetrahydrofuran / 1 h / Heating 2: 5.54 g / quinoline; iodine / benzene / Heating View Scheme

1.1: 97 percent / NaH / tetrahydrofuran / 0 - 20 °C 2.1: 87 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 3.1: 98 percent / PPh3 / CH2Cl2 / 0 - 20 °C 4.1: 86 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 5.1: Cp2ZrCl2; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 5.2: 90 percent / CuCl / tetrahydrofuran; hexane / Heating 6.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 20 °C 7.1: 75 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 99 percent / BH3*THF / tetrahydrofuran / 0 - 20 °C 2.1: 97 percent / NaH / tetrahydrofuran / 0 - 20 °C 3.1: 87 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 4.1: 98 percent / PPh3 / CH2Cl2 / 0 - 20 °C 5.1: 86 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 6.1: Cp2ZrCl2; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 6.2: 90 percent / CuCl / tetrahydrofuran; hexane / Heating 7.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 20 °C 8.1: 75 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: Cp2ZrCl2; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 1.2: 90 percent / CuCl / tetrahydrofuran; hexane / Heating 2.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 20 °C 3.1: 75 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h / 20 °C View Scheme

1: 96 percent / TBAF / tetrahydrofuran / 3 h / 20 °C 2: 75 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h / 20 °C View Scheme

1: 86 percent / NBS; AIBN / CCl4 / Heating 2: 8.66 g / H2O; CaCO3 / 24 h / Heating 3: 100 percent / Pd(PPh3)2Cl2; Et3N; CuI / Heating 4: 97 percent / tetrahydrofuran / 3 h / -78 °C 5: Et3N / tetrahydrofuran / 0 - 20 °C 6: 0.70 g / LiEt3BH / tetrahydrofuran / 18 h / 60 °C 7: 77 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / CH2Cl2 / 6 h / Heating View Scheme

1: 100 percent / Pd(PPh3)2Cl2; Et3N; CuI / Heating 2: 97 percent / tetrahydrofuran / 3 h / -78 °C 3: Et3N / tetrahydrofuran / 0 - 20 °C 4: 0.70 g / LiEt3BH / tetrahydrofuran / 18 h / 60 °C 5: 77 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / CH2Cl2 / 6 h / Heating View Scheme

1: 8.66 g / H2O; CaCO3 / 24 h / Heating 2: 100 percent / Pd(PPh3)2Cl2; Et3N; CuI / Heating 3: 97 percent / tetrahydrofuran / 3 h / -78 °C 4: Et3N / tetrahydrofuran / 0 - 20 °C 5: 0.70 g / LiEt3BH / tetrahydrofuran / 18 h / 60 °C 6: 77 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / CH2Cl2 / 6 h / Heating View Scheme