Crystalline copper Schiff base complexes of general formula [CuL1NO3]n (1) and [CuL2Cl] (2) (where HL1 = 1-[(3-dimethylaminopropylimino)-methyl]-naphthalen-2-ol and HL2 = 3-[(3-dimethylamino-2,2-dimethyl-propylimino)-methyl]-naphthalen-2-ol) were prepared and well characterized. The guest, metal complexes were entrapped in the supercages of NaY zeolite (host) in the solvent phase through two stage process (i) ion exchange of the selected transition metal (Cu(II)-salt) in the porous structure and (ii) encapsulation of Schiff-base ligands (HL1/HL2) in Cu(II) exchanged zeolite. The novel Cu(II) complexes as well as host-guest catalysts were characterized using various physicochemical [Single crystal XRD, elemental analysis, EDX, scanning electron microscopy (FE-SEM), the Brunauer-Emmet-Teller (BET) adsorption technique (N2 gas), Inductively coupled plasma (ICP-MS), powder X-ray diffraction (PXRD), thermal analysis (TGA), cyclic voltametry] and spectroscopic techniques [1H and 13C NMR, FT-IR, ESI-MS, electro spin resonance (ESR), diffuse reflectance spectroscopy (DRS), FT-Raman and GC-MS]. Herein, this study reveals the advantage of heterogeneous catalytic methods for the stability of metal complexes into the supercages of zeolite-Y and the selective oxidation of phenol, styrene and cyclohexene in presence of H2O2 at mild reaction conditions. The catalytic activities of the zeolite entrapped Cu(II) complexes were tested with their homogeneous analogous as well. The heterogeneous catalyst can be re-used after recovering for several cycles without decay of activity which was confirmed by PXRD, cyclic voltammetry, SEM and FTIR studies. © 2018 Elsevier Inc.