Remote desaturation of hexenenitriles by radical-mediated cyano migration. (26th January 2023)

• Record Type: Journal Article
• Authors: Wang, Ziqiang; Chang, Chenyang; Chen, Yasu; Wu, Xinxin; Li, Jie; Zhu, Chen
• Is Part Of: Tetrahedron. Volume 131(2023)
• Publication Date: 2023-01-26
• Subjects: Alkene difunctionalization -- Cyano migration -- Photochemistry -- Radical reactions -- Desaturation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.133228
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: We report a new reaction mode involving functional group migration, which is applied to the radical-mediated remote desaturation of hexenenitriles. The reaction proceeds through consecutive alkene sulfonylation, intramolecular cyano migration, and single-electron oxidation of benzyl radical to cation followed by deprotonation, leading to a variety of densely functionalized alkenes. The protocol features mild photocatalytic conditions, broad functional group tolerance, and high product diversity. Graphical abstract: Image 1