A general route to fluorinated 3, 3-disubstituted 2-oxindoles via a photoinduced radical cyclization of N-arylacrylamides under catalyst-free conditions. Issue 5 (9th March 2016)

• Record Type: Journal Article
• Authors: An, Yuanyuan; Li, Yuewen; Wu, Jie
• Is Part Of: Organic chemistry frontiers. Volume 3:Issue 5(2016:May.)
• Page Start: 570
• Page End: 573
• Publication Date: 2016-03-09
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00055j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A catalyst-free radical cyclization of N -arylacrylamides with fluorinated alkyl iodides or the Togni reagent enabled by photoenergy is reported, leading to fluorinated 2-oxindoles in good yields. The broad reaction scope is demonstrated with good functional group tolerance. Abstract : A catalyst-free radical cyclization of N -arylacrylamides with fluorinated alkyl iodides or the Togni reagent enabled by photoenergy is presented for the first time. Under ultraviolet irradiation, the generation of fluorinated 3, 3-disubstituted 2-oxindoles proceeds smoothly without any metals or photoredox catalysts. The broad reaction scope is demonstrated with good functional group tolerance. During the process, fluorinated alkyl groups can be easily incorporated.