1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.25 h; 2: With iodine in tetrahydrofuran; hexane T=-78 - 20°C;

1: tris(1-methylethyl)(prop-1-yn-1-yl)silane With n-butyllithium in tetrahydrofuran; hexane T=-78°C; Metallation; 2.5 h; 2: 2-(Bromomethyl)-1-iodonaphthalene in tetrahydrofuran; hexane T=-78°C; Substitution; 2.5 h;

1.1: n-BuLi / hexane; tetrahydrofuran / 2.5 h / -78 °C 1.2: 91 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 98 percent / I2 / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1.1: n-BuLi / hexane; tetrahydrofuran / 2.5 h / -78 °C 1.2: 91 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 98 percent / I2 / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 71 percent / tetrahydrofuran / 3 h / -78 °C 2: 92 percent / n-BuLi, I2 / tetrahydrofuran / 1 h View Scheme

1.1: 94 percent / PBr3 / tetrahydrofuran / 1 h / 0 °C 2.1: BuLi / hexane; tetrahydrofuran / 2.5 h / -78 °C 2.2: 69 percent / hexane; tetrahydrofuran / 2.5 h / -78 °C View Scheme