Quinoline is an important natural heterocycle with a structural framework which is common to various bioactive molecules . As shown in Fig. , multiply substituted quinolines serve as privileged scaffolds in many synthetic therapeutics with a wide array of physiological attributes as potential anticancer , antiviral , antifibrotic 10 , antimalarial , and anti-inflammatory drugs . Moreover, poly-substituted quinolines have unique applications as agrochemicals (pyrroloquinoline quinone) , electroluminescent materials (8-hydroxyquinoline) , and dyestuffs (quinoline yellow) . To date, the methods proposed for the synthesis of multiply substituted quinolines include the [4+2] cycloaddition of aromatic imines and methyl propiolate, cyclisation of 2-aminobenzaldehyde and cyclohexane-1,3-dione, etc., or substitution reactions on existing quinoline scaffolds (Scheme 1). However, these methods have disadvantages, such as expensive and dangerous materials, non-green solvents, multi-step process, and high temperature. For example, the method of Xiaochen Ji et al uses nobel metal palladium and methyl acrylate, which is toxic and stinky . As far as Mandeep Kaur's method is concerned, bimetallic Au-Fe3O4 Nano-Hybrid is expensive, and methyl propiolate is toxic, corrosive and highly irritating . CF3-ynones is not a cheap and easily available reagent, and its preparation usually requires a complex process . The method of J. Zeng et al need to use Grignard reagent and Ti(OEt)4, which are hazardous and moisture sensitivity . The method of Masayuki Wasa et al needs high temperature and uses noble metal Pd0 and PCy2tBu-HBF4, the latter is skin corrosive /irritant . Similarly, the method of Adam J. S. J. el al uses noble metal contained catalyst cataCXium A-Pd-G3, and needs high temperature too . The methods of Pin Xu et al uses formamid and large amount of hydrochloric acid. Formamid is hygroscopic, flammable and can strongly corrode copper, brass, lead and rubber . Coupling of O-Acyl Oximes with Isatins to generate quinoline-4-carboxamides needs high temperature and the use of toxic solvent toluene . Therefore, it is essential to explore facile, effective, and green synthetic methods for these unique compounds that have several potential applications in diverse fields of interest. Herein, we present a productive scheme for the synthesis of two quinolines from a singular substrate via exploiting the duality of free radicals under the synergistic catalysis of light and non-noble metal copper salts. Free radicals are highly reactive species containing unpaired electrons. Their chemistry plays a key role in organic syntheses, as many transformations, which are not possible via ionic chemistry, can be readily accomplished via free-radical reactions . However, depending on its molecular structure, a free radical can only participate in either a nucleophilic or an electrophilic reaction. Over the years, various theoretical studies have been attempted to characterise the properties of free radicals and predict their electrophilic-nucleophilic bias in chemical reactions . For example, Pérez et al. have introduced a set of density functional theory (DFT) reactivity indices to determine the electrophilicity or nucleophilicity of a free radical .