potassium carbonate; palladium diacetate in water; N,N-dimethyl-formamide T=20°C; P=760 Torr;

1.1: 91 percent / iodine monochloride; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 1 h / 20 °C 2.1: Mg / tetrahydrofuran / -78 °C 2.2: 77 percent / tetrahydrofuran / 1 h / -78 °C 3.1: 59 percent / formic acid / CH2Cl2 / 2 h / 20 °C 4.1: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 5.1: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme

1.1: Mg / tetrahydrofuran / -78 °C 1.2: 77 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 59 percent / formic acid / CH2Cl2 / 2 h / 20 °C 3.1: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 4.1: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme

1: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 2: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme

1: 59 percent / formic acid / CH2Cl2 / 2 h / 20 °C 2: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 3: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme

1.1: sulfuric acid / 6 h / 80 °C 2.1: 31.4 g / CH2Cl2 / 20 °C 3.1: 72 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 4.2: 56 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C 5.1: 91 percent / iodine monochloride; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 1 h / 20 °C 6.1: Mg / tetrahydrofuran / -78 °C 6.2: 77 percent / tetrahydrofuran / 1 h / -78 °C 7.1: 59 percent / formic acid / CH2Cl2 / 2 h / 20 °C 8.1: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 9.1: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme

1.1: 31.4 g / CH2Cl2 / 20 °C 2.1: 72 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 3.2: 56 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C 4.1: 91 percent / iodine monochloride; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 1 h / 20 °C 5.1: Mg / tetrahydrofuran / -78 °C 5.2: 77 percent / tetrahydrofuran / 1 h / -78 °C 6.1: 59 percent / formic acid / CH2Cl2 / 2 h / 20 °C 7.1: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 8.1: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme

1.1: 72 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 2.2: 56 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.1: 91 percent / iodine monochloride; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 1 h / 20 °C 4.1: Mg / tetrahydrofuran / -78 °C 4.2: 77 percent / tetrahydrofuran / 1 h / -78 °C 5.1: 59 percent / formic acid / CH2Cl2 / 2 h / 20 °C 6.1: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 7.1: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: 56 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.1: 91 percent / iodine monochloride; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 1 h / 20 °C 3.1: Mg / tetrahydrofuran / -78 °C 3.2: 77 percent / tetrahydrofuran / 1 h / -78 °C 4.1: 59 percent / formic acid / CH2Cl2 / 2 h / 20 °C 5.1: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 6.1: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme