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Issue 26, 2020
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Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines

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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.

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

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Supplementary files

Article information


Submitted
29 Jan 2020
Accepted
26 Feb 2020
First published
26 Feb 2020

Chem. Commun., 2020,56, 3777-3780
Article type
Communication

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

D. Liang, L. Tan, W. Xiao and J. Chen, Chem. Commun., 2020, 56, 3777
DOI: 10.1039/D0CC00747A

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