1.1: t-BuLi / diethyl ether; hexane / 0.25 h / -78 °C 1.2: diethyl ether; hexane / -78 - 25 °C 2.1: 0.470 g / PCC / CH2Cl2 / 12 h / 25 °C 3.1: 53 percent / NaOAc / PdCl2(PPh3)2 / N,N-dimethyl-acetamide / 0.02 h / Irradiation View Scheme

n-butyllithium; tributyltin chloride in tetrahydrofuran -100 deg C, 1 h, the -> r.t., 1 h;

n-butyllithium; trimethylstannyl chloride in tetrahydrofuran; hexane -78 deg C, 45 min, then -> r.t., 15 min; other reag.; Product distribution;