1: With titanium(IV) isopropylate; isopropylmagnesium chloride 2: With iodine in tetrahydrofuran T=-50°C;

b-Bu4NF in tetrahydrofuran T=-78°C; 2 h;

1: anhydrous 1-octyne With iso-propylmagnesium bromide in tetrahydrofuran T=20°C; 2 h; 2: (1Z,3Z)-1,4-diiodo-2-hexyl-1-(trimethylsilyl)-1,3-decadiene With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; 12 h;

1.1: 76 percent / b-Bu4NF / tetrahydrofuran / 2 h / -78 °C 2.1: isopropylmagnesium bromide / tetrahydrofuran / 2 h / 20 °C 2.2: Pd(PPh3)4 / tetrahydrofuran / 12 h / 20 °C View Scheme

1.1: isopropylmagnesium bromide / tetrahydrofuran / 2 h / 20 °C 1.2: Pd(PPh3)4 / tetrahydrofuran / 12 h / 20 °C 2.1: 76 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C View Scheme