A new and efficient oxo-sulfonylation protocol has been established for the synthesis of N-sulfonylated indazolones employing sulfinic acid as a sulfonylating agent using tert-butyl hydroperoxide (TBHP) under ambient air. A series of structurally diverse 1-sulfonylindazol-3(2H)-one derivatives were obtained in good yields. A radical reaction mechanism has been proposed for this transformation.