manganese(IV) oxide in tetrahydrofuran 1 h;

Schwartz's reagent; dimethylaluminum chloride in dichloromethane T=0°C;

tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; [Ph2PO2]1-*[NBu4]1+ in 1-methyl-pyrrolidin-2-one T=45°C; Stille coupling; 1.66667 h; Inert atmosphere;

tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; [Ph2PO2]1-*[NBu4]1+ in 1-methyl-pyrrolidin-2-one T=45°C; Stille coupling; 3 h; Inert atmosphere;

in toluene Heating;

1: PdCl2(PhCN)2, CuI, piperidine / 1 h / Ambient temperature 2: 79 percent / Red-Al / tetrahydrofuran; toluene / Ambient temperature 3: 80 percent / MnO2 / CH2Cl2 / 1 h View Scheme

1: 79 percent / Red-Al / tetrahydrofuran; toluene / Ambient temperature 2: 80 percent / MnO2 / CH2Cl2 / 1 h View Scheme

1: 1.) methanesulfonyl chloride, triethylamine, 2.) DBU / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature 2: PdCl2(PhCN)2, CuI, piperidine / 1 h / Ambient temperature 3: 79 percent / Red-Al / tetrahydrofuran; toluene / Ambient temperature 4: 80 percent / MnO2 / CH2Cl2 / 1 h View Scheme

1: 79 percent / Red-Al / diethyl ether; toluene / 5 h / -20 - 36 °C 2: 1.) methanesulfonyl chloride, triethylamine, 2.) DBU / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature 3: PdCl2(PhCN)2, CuI, piperidine / 1 h / Ambient temperature 4: 79 percent / Red-Al / tetrahydrofuran; toluene / Ambient temperature 5: 80 percent / MnO2 / CH2Cl2 / 1 h View Scheme

1: 82 percent / PdCl2(PPh3)2, CuI, piperidine / diethyl ether / 4 h / 15 - 20 °C 2: 79 percent / Red-Al / diethyl ether; toluene / 5 h / -20 - 36 °C 3: 1.) methanesulfonyl chloride, triethylamine, 2.) DBU / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature 4: PdCl2(PhCN)2, CuI, piperidine / 1 h / Ambient temperature 5: 79 percent / Red-Al / tetrahydrofuran; toluene / Ambient temperature 6: 80 percent / MnO2 / CH2Cl2 / 1 h View Scheme