1: 72 percent / 1,10-phenanthroline; CuI; Cs2CO3 / 48 h / 120 °C 2: 100 percent / HCO2NH4 / Pd/C / acetone / 72 h / Heating View Scheme

1: 1-iodo-propane With manganese bromide tetrahydrate; N,N'-dimethyl-N,N'-propyleneurea; diethylzinc; copper(l) chloride in tetrahydrofuran T=20°C; 4 h; 2: 3-benzyloxy-iodobenzene With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct in tetrahydrofuran 2.5 h; Heating / reflux;

1: ethyl iodide With manganese bromide tetrahydrate; N,N'-dimethyl-N,N'-propyleneurea; diethylzinc; copper(l) chloride in tetrahydrofuran 4 h; 2: 3-benzyloxy-iodobenzene With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct in tetrahydrofuran 2.5 h; Heating / reflux; Product distribution / selectivity;

1: 88 percent / 1,10-phenanthroline; CuI; Cs2CO3 / 48 h / 120 °C 2: 100 percent / HCO2NH4 / Pd/C / acetone / 72 h / Heating View Scheme

1: 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester With chloro-trimethyl-silane; ethylene dibromide; zinc in N,N-dimethyl-formamide T=20 - 70°C; 2.16667 h; 2: 3-benzyloxy-iodobenzene With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane in N,N-dimethyl-formamide T=70°C; 4 h;