Citation: LI Zengzeng, YUAN Li, WANG Liangneng, WANG Shuowen, YU Jian, XIA Lyulu, DENG Youlin, TANG Shi. Visible Light Induced Desulfonylative Annulation Cascade of N-Sulfonylmethacrylamides[J]. Chinese Journal of Applied Chemistry, ;2017, 34(11): 1287-1294. doi: 10.11944/j.issn.1000-0518.2017.11.170054 shu

Visible Light Induced Desulfonylative Annulation Cascade of N-Sulfonylmethacrylamides

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

Corresponding author: TANG Shi, stang@jsu.edu.cn
Received Date: 1 March 2017
Revised Date: 10 April 2017
Accepted Date: 8 May 2017

Fund Project: Supported by the National Natural Science Foundation of China(No.21462017, No.21662013), the Research Innovation Program for Graduates of Jishou University(No.JGY201636), the Research Program for Graduates of Science and Technology Department of Jishou University(No.JDY16018)the National Natural Science Foundation of China 21662013the Research Program for Graduates of Science and Technology Department of Jishou University JDY16018the National Natural Science Foundation of China 21462017the Research Innovation Program for Graduates of Jishou University JGY201636

Figures(3)

A visible light induced desulfonylative cyclization cascade of N-sulfonylmethacrylamides toward perfluoroalkylated oxindoles and α-arylamides was developed. Under light-emitting diode(LED) irradiation, in the presence of fac-tris-2-phenylpyridine iridium(Ⅲ)(fac-Ir(ppy)₃) and perfluoroalkyl iodides or bromides, N-butyl-N-(tolylsulfonyl)methacrylamides underwent tandem radical addition/β-arylmigration/desulfonylation to construct two-fold of C-C bonds in single step, leading to a series of perfluoroalkylated oxindoles and α-aryl-β-perfluoroalkyl amide in 41%~78% yield. This mild catalytic protocol exhibits a broad substrate scope and therefore, provides a green and efficient approach to fluorinated oxindoles with potential biological activities.
- N-sulfonylmethacrylamides,
- perfluoroalkylation,
- cascade cyclization,
- photoredox catalysis,
- oxindoles
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