4.8 Article

Visible-Light Photoredox-Catalyzed Iminyl Radical Formation by N-H Cleavage with Hydrogen Release and Its Application in Synthesis of Isoquinolines

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ORGANIC LETTERS
卷 20, 期 5, 页码 1421-1425

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00193

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  1. 111 Project of MOE [111-2- 17]
  2. Fundamental Research Funds for the Central Universities [xjj2015099]
  3. NSFC [21472145, 21572085]

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An unprecedented visible-light photoredox-catalyzed iminyl radical formation by N-H cleavage with H-2 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 CIO4-, 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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