lithium diisopropyl amide in tetrahydrofuran Ambient temperature;

1: 80 percent / O2, PdCl2, CuCl / dimethylformamide; H2O 2: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) 0 deg C, 5 h 3: 80 percent / O32, PdCl2, CuCl 4: 14 percent / LDA / tetrahydrofuran / Ambient temperature View Scheme

1: 100 percent / p-TsOH / benzene / Heating 2: 80 percent / O2, PdCl2, CuCl / dimethylformamide; H2O 3: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) 0 deg C, 5 h 4: 80 percent / O32, PdCl2, CuCl 5: 14 percent / LDA / tetrahydrofuran / Ambient temperature View Scheme

1: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) 0 deg C, 5 h 2: 80 percent / O32, PdCl2, CuCl 3: 14 percent / LDA / tetrahydrofuran / Ambient temperature View Scheme

1: 80 percent / O32, PdCl2, CuCl 2: 14 percent / LDA / tetrahydrofuran / Ambient temperature View Scheme