Visible Light Induced Desulfonylative Annulation Cascade of N-Sulfonylmethacrylamides

doi:10.11944/j.issn.1000-0518.2017.11.170054

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (11): 1287-1294.DOI: 10.11944/j.issn.1000-0518.2017.11.170054

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Visible Light Induced Desulfonylative Annulation Cascade of N-Sulfonylmethacrylamides

LI Zengzeng,YUAN Li,WANG Liangneng,WANG Shuowen,YU Jian,XIA Lyulu,DENG Youlin,TANG Shi()

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

Received:2017-03-01 Accepted:2017-05-08 Published:2017-11-08 Online:2017-11-08
Contact: TANG Shi
Supported by:
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)

Abstract

Abstract:

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.

Key words: N-sulfonylmethacrylamides, perfluoroalkylation, cascade cyclization, photoredox catalysis, oxindoles

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.

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Visible Light Induced Desulfonylative Annulation Cascade of N-Sulfonylmethacrylamides

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