1: With lithium diisopropyl amide in tetrahydrofuran; hexane T=-75°C; 2 h; 2: With iodine in tetrahydrofuran; hexane

1.1: 87 percent / sodium iodide; chlorotrimethylsilane / various solvent(s) / 6 h / Heating 2.1: 72 percent / potassium fluoride; cuprous iodide; N-methylpyrrolidinone 3.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -75 °C 3.2: 87 percent / iodine / hexane; tetrahydrofuran View Scheme

1.1: 72 percent / potassium fluoride; cuprous iodide; N-methylpyrrolidinone 2.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -75 °C 2.2: 87 percent / iodine / hexane; tetrahydrofuran View Scheme

lithium diisopropyl amide in tetrahydrofuran; hexane T=-75°C; 2 h;