Synthesis of Perfluorinated Isoquinolinediones through Visible-Light-Induced Cyclization of Alkenes

Shi Tang; You-Lin Deng; Jie Li; Wen-Xin Wang; Guo-Liang Ding; Ming-Wei Wang; Zhu-Ping Xiao; Ying-Chun Wang; Rui-Long Sheng

doi:10.1021/acs.joc.5b01803

Synthesis of Perfluorinated Isoquinolinediones through Visible-Light-Induced Cyclization of Alkenes

J Org Chem. 2015 Dec 18;80(24):12599-605. doi: 10.1021/acs.joc.5b01803. Epub 2015 Dec 1.

Authors

Shi Tang^{1

2}, You-Lin Deng¹, Jie Li¹, Wen-Xin Wang¹, Guo-Liang Ding¹, Ming-Wei Wang¹, Zhu-Ping Xiao¹, Ying-Chun Wang¹, Rui-Long Sheng³

Affiliations

¹ College of Chemistry and Chemical Engineering, Jishou University , Jishou 416000, China.
² College of Chemistry and Chemical Engineering, Central South University , Changsha 410083, China.
³ Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

PMID: 26580021
DOI: 10.1021/acs.joc.5b01803

Abstract

A novel visible-light-induced carboperfluoroalkylation of alkenes using perfluoroalkyl iodides and bromides as Rf sources, leading to isoquinoline-1,3-diones, was developed. This method offers rapid entry to perfluorinated isoquinoline-1,3(2H,4H)-diones from N-alkyl-N-methacryloyl benzamides under mild reaction conditions, allowing for the incorporation of a wide variety of perfluorinated groups such as CF3, C3F7, C4F9, C6F13, C8F17, C10F21, and CF2CO2Et.

Publication types

Research Support, Non-U.S. Gov't