N-methyl-2-indolinone; tetrapropylammonium perruthennate

1.1: 65 percent / Cu(OTf)2 / acetonitrile / 0.25 h / 20 °C 2.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 2.2: 89 percent / aqueous sodium hydroxide; aqueous hydrogen peroxide / tetrahydrofuran / 2 h / 20 °C 3.1: 74 percent / triethylamine; sulfur trioxide-pyridine complex / CH2Cl2; dimethylsulfoxide / 3 h / 0 °C View Scheme

1.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 1.2: 89 percent / aqueous sodium hydroxide; aqueous hydrogen peroxide / tetrahydrofuran / 2 h / 20 °C 2.1: 74 percent / triethylamine; sulfur trioxide-pyridine complex / CH2Cl2; dimethylsulfoxide / 3 h / 0 °C View Scheme