1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - -30°C; 2 h; 3: With hydrogenchloride; water in tetrahydrofuran; hexane

1: 2-bromo-3,4-dimethyl-2-cyclopenten-1-one ethylene ketal With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - -30°C; 2 h; 3: With hydrogenchloride in tetrahydrofuran; hexane; water

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water T=95°C; Suzuki-coupling reaction; 12 h;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water T=95°C; Suzuki-coupling reaction; 12 h;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water T=95°C; Suzuki-coupling reaction; 12 h;

1: 87 percent / Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 12 h / 95 °C 2: 89 percent / CeCl3 / tetrahydrofuran; diethyl ether / 2 h / -78 °C View Scheme

1: 74 percent / Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 12 h / 95 °C 2: 75 percent / CeCl3 / tetrahydrofuran; diethyl ether / 2 h / -78 °C View Scheme