Visible-Light Photoredox-Catalyzed Iminyl Radical Formation by N–H Cleavage with Hydrogen Release and Its Application in Synthesis of Isoquinolines
journal contributionposted on 16.02.2018, 16:21 by Wan-Fa Tian, Dang-Po Wang, Shao-Feng Wang, Ke-Han He, Xiao-Ping Cao, Yang Li
An unprecedented visible-light photoredox-catalyzed iminyl radical formation by N–H cleavage with H2 release has been developed. Its application in the synthesis of various isoquinolines and related polyaromatics in high atom economy at ambient temperature by applying a photosensitizer, Acr+-Mes ClO4–, and a new cobalt catalyst, Co(dmgH)2(4-CONMe2Py)Cl is reported. Mechanistic investigations indicated that the generated iminyl radical initiates the cascade C–N/C–C bonds formation and the catalytic cycle occurs by a simultaneous oxidative as well as reductive quenching pathway.
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Acratom economyPyambient temperatureApplicationoxidativesynthesisClOphotosensitizerapplicationIsoquinolineH 2 releaseSynthesireductive quenching pathwaypolyaromaticformationvisible-light photoredox-catalyzed iminylCleavagecobalt catalystCoisoquinolineCONMecascadeHydrogen ReleaseMechanistic investigationscleavageVisible-Light Photoredox-Catalyzed Iminyl Radical Formationbond