tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triethylamine; triphenylphosphine in tetrahydrofuran 14 h; Heating;

1: 90 percent / Me4NIO4 / CH2Cl2 / 1.5 h / Ambient temperature 2: 90 percent / 45percent HBr(AcOH) / 2 h / Ambient temperature 3: 64 percent / Zn, AcOH / 4 h / 50 - 60 °C 4: 1.) NaH / 1.) Et2O, r. t., 2 h, 2.) r. t., 2 h 5: 93 percent / pyridine / CH2Cl2 / 2 h / 0 °C 6: 64 percent / NEt3, Ph3P, Pd2(dba)3*CHCl3 / tetrahydrofuran / 14 h / Heating View Scheme

1: 90 percent / 45percent HBr(AcOH) / 2 h / Ambient temperature 2: 64 percent / Zn, AcOH / 4 h / 50 - 60 °C 3: 1.) NaH / 1.) Et2O, r. t., 2 h, 2.) r. t., 2 h 4: 93 percent / pyridine / CH2Cl2 / 2 h / 0 °C 5: 64 percent / NEt3, Ph3P, Pd2(dba)3*CHCl3 / tetrahydrofuran / 14 h / Heating View Scheme

1: 1.) NaH / 1.) Et2O, r. t., 2 h, 2.) r. t., 2 h 2: 93 percent / pyridine / CH2Cl2 / 2 h / 0 °C 3: 64 percent / NEt3, Ph3P, Pd2(dba)3*CHCl3 / tetrahydrofuran / 14 h / Heating View Scheme

1: 64 percent / Zn, AcOH / 4 h / 50 - 60 °C 2: 1.) NaH / 1.) Et2O, r. t., 2 h, 2.) r. t., 2 h 3: 93 percent / pyridine / CH2Cl2 / 2 h / 0 °C 4: 64 percent / NEt3, Ph3P, Pd2(dba)3*CHCl3 / tetrahydrofuran / 14 h / Heating View Scheme

1: 93 percent / pyridine / CH2Cl2 / 2 h / 0 °C 2: 64 percent / NEt3, Ph3P, Pd2(dba)3*CHCl3 / tetrahydrofuran / 14 h / Heating View Scheme

1: 90 percent / Me4NIO4 / CH2Cl2 / 1.5 h / Ambient temperature 2: 7 percent / Na/Hg, Na2HPO4 / ethanol / 2 h / Ambient temperature 3: 93 percent / pyridine / CH2Cl2 / 2 h / 0 °C 4: 64 percent / NEt3, Ph3P, Pd2(dba)3*CHCl3 / tetrahydrofuran / 14 h / Heating View Scheme