A highly efficient oxidative dearomatization of indoles with H-phosphorus oxides in the presence of TEMPO oxoammonium salt has been demonstrated. Through the intramolecular oxidative dearomatization of indoles and subsequent intermolecular nucleophilic addition with phosphorus nucleophile, a variety of structurally diverse arylphosphoryl and alkylphosphoryl indolin-3-ones were obtained in good yields with a broad substrate scope and high functional-group compatibility.