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Graphical abstract Highlights • 3,3-Disubstituted isoindolin-1-ones were prepared by radical addition and cyclization in moderate to good yields. • Toluene derivatives were used as radical precursors and two new C–C bonds were formed in one step. • The reactions were carried out under environmentally friendly conditions with excellent atom economy. Abstract Copper(I) catalyzed radical benzylation and cyclization reaction of tertiary enamides was investigated and 3,3-disubstituted N-Alkyl isoindolin-1-ones were obtained in moderate to good yields. In this reaction, two new C–C bonds were formed in one step with high atom economy. Possible reaction pathway for the formation of the products was also discussed in this paper. [ABSTRACT FROM AUTHOR]