化学
光化学
卤素
肉桂醇
密度泛函理论
反应机理
催化作用
组合化学
有机化学
烷基
计算化学
选择性
作者
Roshan K. Dhungana,Albert Granados,Vittorio Ciccone,R. Torrence Martin,Jadab Majhi,Mohammed Sharique,Osvaldo Gutiérrez,Gary A. Molander
标识
DOI:10.1021/acscatal.2c05514
摘要
A photochemical synthesis of brominated α,α-difluoro-γ-lactones from cinnamyl alcohols and ethyl bromodifluoroacetate is reported via one-pot Giese addition/lactonization/halogen-atom transfer (XAT) processes. This transformation provides brominated α,α-difluoro-γ-lactones in moderate to good diastereoselectivities. The reaction affords a rapid increase in molecular complexity in organofluorine chemical space. Dispersion-corrected density functional theory (DFT) calculations and experiments support a lactonization-induced radical chain mechanism in which a long-lived radical intermediate undergoes a diastereoselective halogen-atom transfer to restart the radical chain cycle.
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