Work

Photocatalytic redox-neutral selective single C(sp 3 )–F bond activation of perfluoroalkyl iminosulfides with alkenes and water

Year: 2023

Type: article

Abstract: Visible-light-promoted site-selective and direct C − F bond functionalization of polyfluorinated iminosulfides were accomplished with alkenes and water under redox-neutral conditions, affording a diverse array of mutifluorinated γ-lactams. A variety of perfluoroalkyl units included C2F5, C3F7, C4F9and C5F11underwent site-selective defluorofunctionlization. This protocol allows high chemoselectivity control and shows excellent functional group tolerance. Mechanistic studies reveal that the remarkable changes of the electron geometries during the defluorination widen the redox window between the substrates and the products and ensure the chemoselectivity of single C(sp3) − F bond cleavage.

Source: Chemical Science

DOI: 10.1039/d3sc03771a

Authors: Tao Wang, Yuan-Yuan Zong, Tao Huang, Xiao-Ling Jin, Li-Zhu Wu, Qiang Liu

Institutions: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Chinese Academy of Sciences, Technical Institute of Physics and Chemistry

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Natural Science Foundation of China, Science and Technology Department of Gansu Province

Awards: G2116894412, G8914618768