Visible‐Light‐Promoted Synthesis of Fluoroalkylated Oximes

• Published in: Chemistry, an Asian journal Vol. 13; no. 17; pp. 2405 - 2409
• Main Authors: Lee, Da Seul, Hwang, Ho Seong, Cho, Eun Jin
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 04.09.2018
• Subjects: Alkenes; Aromatic compounds; Chemistry; fluorine; Light irradiation; nitrites; Organofluorine compounds; Oximes; photocatalysis; radical reactions; Substrates; Synthesis; radical reactions; nitrite; oxime; photocatalysis; fluorine
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201800524

A method has been developed for the synthesis of fluoroalkylated oximes, potential fluoroalkyl building‐blocks for the synthesis of various organofluorine compounds, from easily available amino substrates and fluoroalkylated alkenes. tBuONO was utilized both as a diazotizing agent and as a NO radical source for the oxime synthesis in the process, and the use of a photocatalyst under visible‐light irradiation increased the efficiency of the reaction. Various fluoroalkylated oximes were prepared by a tandem process of aryl radical addition to fluoroalkylated alkene and consecutive oxime generation process, albeit in moderate yields. This differentiated approach, transferring an aromatic system into an electron‐deficient fluoroalkylated alkene, expands the scope of substrates where electron‐poor aromatic systems could be utilized. Just gimme the light: A visible‐light‐promoted tandem process for the synthesis of fluoroalkylated oximes has been developed. This approach could be applied to both electron‐rich/‐deficient aromatic compounds.