Unified Synthesis of Azepines by Visible-Light-Mediated Dearomative Ring Expansion of Aromatic N-Ylides
Matthew J. Mailloux, Gabrielle S. Fleming, Shruti S. Kumta and Aaron B. Beeler*
*Department of Chemistry, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States,
Email: beelera
bu.edu
M. J. Mailloux, G. S. Fleming, S. S. Kumta, A. B. Beeler, Org. Lett., 2021, 23, 525-529.
DOI: 10.1021/acs.orglett.0c04050
see article for more reactions
Abstract
Deprotonation of quaternary aromatic salts with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or N,N,N',N'-tetramethylquanidine (TMG) under visible light irradiation followed by ring-expansion provides mono- and polycyclic functionalized azepines in very good yields. This dearomative photochemical rearrangement uses two straightforward steps and simple starting materials.
see article for more examples
proposed mechanism
While ads financed 62% of the published abstracts in 2024, donations allowed us to publish additional 12%. 26% of the abstracts have been published voluntarly. If you kindly donate, we can publish more freely accessible information and help the chemical community even more:
If you don't like pawalls or a flood of more and more advertising, then you can send a clear signal here!
Key Words
azepines, photochemistry, flow chemistry
ID: J54-Y2021
