Rhodium-Catalyzed One-Pot Access to N-Polycyclic Aromatic Hydrocarbons from Aryl Ketones through Triple C–H Bond Activations

• DOI: 10.1021/acs.joc.0c02582
• Publication Date: 2020-12-18T09:02:29Z
• Authors: Pragati Biswal; Shyam Kumar Banjare; Bedadyuti Vedvyas...; Smruti Ranjan Moh...; Ponneri Chandraba...
• Keywords: Triple bond; Isoquinoline; Alkyne; Hydroxylamine; Cascade reaction

A Rh-catalyzed pot and step economic synthesis of aza-polycyclic aromatic hydrocarbons (N-PAHs) from readily available aryl ketones alkynes has been disclosed. Additionally, a novel synthetic application the well-known aminating reagent hydroxylamine-O-sulfonic acid (HOSA) explored as an in situ redox-neutral directing group for formation N-PAHs via isoquinoline. Multiple bond single operation through cascade triple C–H activations is beauty this protocol. The challenging annulations two different regioselective fashion have demonstrated effectively. Mechanistic studies reveal that 3,4-diphenyl-1-methylisoquinoline active intermediate one-pot transformation.