n-butyllithium in diethyl ether T=25°C;

1.1: cyclohexene; BH3 / pentane / -78 °C 1.2: 80 percent / ethanolamine; AcOH 2.1: Pd(PPh3)4 / benzene / 25 °C 2.2: 90 percent / CuI; Et3N / 30 h / 25 °C 3.1: 86 percent / PPh3Br2 / CH2Cl2; pyridine / from 0 degC to r.t. 4.1: 87 percent / methanol / 100 °C 5.1: 59 percent / n-BuLi / diethyl ether / 25 °C View Scheme

1.1: Pd(PPh3)4 / benzene / 25 °C 1.2: 90 percent / CuI; Et3N / 30 h / 25 °C 2.1: 86 percent / PPh3Br2 / CH2Cl2; pyridine / from 0 degC to r.t. 3.1: 87 percent / methanol / 100 °C 4.1: 59 percent / n-BuLi / diethyl ether / 25 °C View Scheme

1: 86 percent / PPh3Br2 / CH2Cl2; pyridine / from 0 degC to r.t. 2: 87 percent / methanol / 100 °C 3: 59 percent / n-BuLi / diethyl ether / 25 °C View Scheme

1: 87 percent / methanol / 100 °C 2: 59 percent / n-BuLi / diethyl ether / 25 °C View Scheme