Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (4): 424-432.DOI: 10.11944/j.issn.1000-0518.2020.04.190140

• Full Papers • Previous Articles     Next Articles

Visible-Light-Induced Cyclization of 1,n-Enyne and Polyfluoroalkyl Halides Toward Halo-perfluorinated 2,4-Dihydroisoquinoline-2(1H)-one

WANG Shuowen,LIU Yuan,XU Zhenhua,ZENG Rong,CHEN Yi,TANG Shi()   

  1. College of Chemistry and Chemical Engineering,Jishou University,Jishou,Hunan 416000,China
  • Received:2019-05-14 Accepted:2019-07-15 Published:2020-04-01 Online:2020-04-10
  • Contact: TANG Shi
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.21662013), and the Research Program for Graduates of Science and Technology Department of Jishou University(No.Jdy19)

Abstract:

Visible light-induced reaction of 1,7-enyne with perfluoroalkyl halide through a tandem atom transfer radical addition (ATRA)/cyclization sequence, synthesizing fluorinated 2,4-dihydroisoquinoline-2(1H)-one was developed. With polyfluoroalkyl iodine or bromine as the free radical precursor, fac-Ir (ppy)3 (molar fraction 1%) as the photosensitizer, ATRA/cyclization reactions of various benzene-linked 1,7-enyne occurred successfully under 5 W blue light emitting diode (LED) irradiation. A series of polyfluorinated isoquinolone derivatives was synthesized in modorate to excellent yields (62%~84%). This highly efficient synthetic method is mild and clean, providing a new way for the synthesis of polyfluoride 2,4-dihydroisoquinoline-2(1H)-ketone with potential medicinal value.

Key words: visible light induction, atom transfer radical addition, 2,4-dihydroisoquinoline-2(1H)-one, polyfluoroalkylation, enyne