1: With lithium diisopropyl amide in tetrahydrofuran; hexane T=-75°C; 0.75 h; 2: With iodine in tetrahydrofuran; hexane

1-methyl-pyrrolidin-2-one; potassium fluoride; copper(l) iodide T=50°C; 20 h;

1: 64 percent / potassium fluoride; cuprous iodide; N-methylpyrrolidinone / 20 h / 50 °C 2: 68 percent / 2,2,6,6-tetramethylpiperidine; butyllithium / hexane; diethyl ether / 2 h / -75 °C View Scheme

1.1: 64 percent / potassium fluoride; cuprous iodide; N-methylpyrrolidinone / 20 h / 50 °C 2.1: 68 percent / 2,2,6,6-tetramethylpiperidine; butyllithium / hexane; diethyl ether / 2 h / -75 °C 3.1: butyllithium / hexane; toluene / 0.25 h / -75 °C 3.2: 82 percent / hexane; toluene; diethyl ether View Scheme