Citation: WANG Shuowen, LIU Yuan, XU Zhenhua, ZENG Rong, CHEN Yi, TANG Shi. Visible-Light-Induced Cyclization of 1, n-Enyne and Polyfluoroalkyl Halides Toward Halo-perfluorinated 2, 4-Dihydroisoquinoline-2(1H)-one[J]. Chinese Journal of Applied Chemistry, ;2020, 37(4): 424-432. doi: 10.11944/j.issn.1000-0518.2020.04.190140 shu

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

College of Chemistry and Chemical Engineering, Jishou University, Jishou, Hunan 416000, China

Corresponding author: TANG Shi, stang@jsu.edu.cn
Received Date: 14 May 2019
Revised Date: 24 June 2019
Accepted Date: 15 July 2019

Fund Project: the Research Program for Graduates of Science and Technology Department of Jishou University Jdy19Supported 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)the National Natural Science Foundation of China 21662013

Figures(4)

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