Metal-Free C–H Heterofunctionalization of Naphthoquinone via Unprecedented C–N Bond Formation and Cleavage Using Imidazole

Heterofunctionalization is an important tool for synthesis of bioactive molecules and to create new chemical entities. We developed a green and efficient method for the direct C-H/N-H cross dehydrogenative coupling of aryl naphthoquinone with imidazole in the absence of metal, ligand, and additive. Most interestingly, the synthesized imidazoloquinones were utilized as a key intermediate for unprecedented C-S, C-N, and highly valuable C-O bond heterofunctionalization. Important features of present findings, compared to previously known methods, are C-H and C-N bond activation under metal free condition, hetero functionalization of imidazoloquinone, no need for reoxidation, broad substrate scope, and high yields.