Citation: YUAN Li, LI Zengzeng, JIANG Shengming, ZHU Yong, LEI Qian, XIA Lülu, LI Lan, YU Jian, ZHANG Juan, TANG Shi. Visible-Light-Induced Dearomatizing Spirocyclization of Alkenes Toward Perfluorinated Azaspirocyclic Cyclohexadienones[J]. Chinese Journal of Applied Chemistry, ;2018, 35(2): 181-188. doi: 10.11944/j.issn.1000-0518.2018.02.170099 shu

Visible-Light-Induced Dearomatizing Spirocyclization of Alkenes Toward Perfluorinated Azaspirocyclic Cyclohexadienones

College of Chemistry and Chemical Engineering, Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wuling Mountains, Jishou University, Jishou, Hu'nan 416000, China

Corresponding author: TANG Shi, stang@jsu.edu.cn
Received Date: 1 April 2017
Revised Date: 9 May 2017
Accepted Date: 18 May 2017

Fund Project: Supported by the National Natural Science Foundation of China(No.21462017, No.21662013), the Research Innovation Program for Graduates in Hu′nan province(No.16A171)

Figures(4)

A visible-light-induced dearomation cyclilation of N-benzylmethacrylamides with nonafluorinated alkyl bromides or iodides toward nonafluorinated azaspirocyclic cyclo-hexadienones was developed. Under the irradiation of blue light-emitting diode(LED) light, using fac-Ir(ppy)₃(fac=facial, ppy=2-phenylpyridyl) as the photocatalyst, N-benzylmethacrylamides and nonafluorinated alkyl bromides or iodides underwent cascade dearomation/cyclilation under optimal conditions, leading to a series of perfluorinating azaspirocyclic cyclohexadienones in 61%~85% yield, as well as introducing a series of perfluorinated moieties including CF₃, C₃F₇, C₄F₉, C₆F₁₃, C₈F₁₇, CH₂CF₂, CF₂CO₂Et(Et:Ethyl). Given the broad substrate scope, mild reaction conditions and green catalytic systems, this protocol provides a green, effective and quick approach to pharmaceutically important cyclohexadienones.
- perfluorinated,
- dearomative cyclilation,
- visible-light-induced,
- azaspirocyclic cyclohexadienones,
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