Krishna T P Adarsh, Sakthivel Pandaram, Kota Laxman, Kalainilavan Kumaresan, Asokan Kathiravan, Ilangovan Andivelu
School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamilnadu 620024, India.
J Org Chem. 2025 Jun 20;90(24):8013-8026. doi: 10.1021/acs.joc.4c03162. Epub 2025 Jun 6.
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.
