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

Wan-Fa Tian; Dang-Po Wang; Shao-Feng Wang; Ke-Han He; Xiao-Ping Cao; Yang Li

doi:10.1021/acs.orglett.8b00193

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

Org Lett. 2018 Mar 2;20(5):1421-1425. doi: 10.1021/acs.orglett.8b00193. Epub 2018 Feb 16.

Authors

Wan-Fa Tian^{1

2}, Dang-Po Wang^{1

2}, Shao-Feng Wang^{1

2}, Ke-Han He², Xiao-Ping Cao¹, Yang Li²

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, P. R. China.
² Center for Organic Chemistry, Frontier Institute of Science and Technology, Xi'an Jiaotong University , Xi'an, Shaanxi 710054, P. R. China.

PMID: 29451800
DOI: 10.1021/acs.orglett.8b00193

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't