Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines

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 precur...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-04, Vol.56 (26), p.3777-3780
Main Authors: Liang, Dong, Tan, Li-Ping, Xiao, Wen-Jing, Chen, Jia-Rong
Format: Article
Language:English
Subjects:
Cycloaddition
Perfluoro compounds
Perfluoroalkyl & polyfluoroalkyl substances
Quinones
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc00747a