Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-<i>ortho</i>-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines
Dong Liang, Li-Ping Tan, Wen‐Jing Xiao, Jia‐Rong Chen
Abstract
A [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with formaldimines is described for the synthesis of perfluoroalkylated tetrahydroquinazolines. Key to this process is the photocatalytic radical-mediated generation of aza-o-QMs from 2-vinylanilines and perfluoroalkyl radical precursors as well as the in situ release of formaldimines from 1,3,5-triazinanes.
Topics & Concepts
CycloadditionChemistryQuinonePhotocatalysisPhotochemistryOrganic chemistryCatalysisSynthesis of Indole DerivativesFluorine in Organic ChemistrySulfur-Based Synthesis Techniques