Herein, we report a unified approach to azepines by dearomative photochemical rearrangement of aromatic -ylides. Deprotonation of quaternary aromatic salts with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or -tetramethylquanidine (TMG) under visible light irradiation provides mono- and polycyclic azepines in yields up to 98%. This ring-expansion presents a new mode of access to functionalized azepines from N-heteroarenes using two straightforward steps and simple starting materials.
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| http://dx.doi.org/10.1021/acs.orglett.0c04050 | DOI Listing |
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