B4NF*3H2O in tetrahydrofuran T=25°C; 0.5 h;

n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-75°C; 2 h;

1.1: secBuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C 1.2: 92 percent / tetrahydrofuran; cyclohexane / -75 °C 2.1: secBuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C 2.2: 95 percent / Br2 / tetrahydrofuran; cyclohexane / -75 °C 3.1: 85 percent / (iPr)2NH; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C View Scheme

1.1: secBuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C 1.2: 92 percent / tetrahydrofuran; cyclohexane / -75 °C 2.1: secBuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C 2.2: 95 percent / Br2 / tetrahydrofuran; cyclohexane / -75 °C 3.1: 85 percent / (iPr)2NH; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C View Scheme

1.1: secBuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C 1.2: 95 percent / Br2 / tetrahydrofuran; cyclohexane / -75 °C 2.1: 85 percent / (iPr)2NH; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C View Scheme