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This article proposes a milder approach for C(sp2=−H functionalization of 2,2‐disubstituted cyclopentene‐1,3‐dione via formal 1° amination utilizing water as a solvent. In addition, this approach also offers C(sp2)−O, C(sp2)−I bond formation for the first time using sodium azide. The said highly scalable transformation does not require any prefunctionalization of the starting material. Moreover, this methodology is metal free, requires no ligand and all these reactions are carried out in an open‐air atmosphere with broad substrate scope. We have also explored a novel BF3.OEt2 mediated dehalogenation using mild reaction conditions. [ABSTRACT FROM AUTHOR]