articleJournal of the American Chemical SocietyMay 26, 2023Closed access

ortho -Selective Dearomative [2π + 2σ] Photocycloadditions of Bicyclic Aza-Arenes

University of Münster · University of California, Los Angeles

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Abstract

Dearomative photocycloadditions are valuable chemical transformations, serving as an efficient platform to create three-dimensional molecular complexity. However, the photolability of the original addition product especially within the context of ortho cycloadditions often causes undesired consecutive rearrangements, rendering these ortho cycloadducts elusive. Herein, we report an ortho-selective intermolecular photocycloaddition of bicyclic aza-arenes including (iso)quinolines, quinazolines, and quinoxalines by utilizing a strain-release approach. With bicyclo[1.1.0]butanes as coupling partners, this dearomative [2π + 2σ] cycloaddition enables the straightforward construction of C(sp3)-rich…

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205
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FWCI
29.21
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100%
References
102
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Authors

10

Topics & keywords

Keywords
  • Bicyclic molecule
  • Chemistry
  • Cycloaddition
  • Intermolecular force
  • Context (archaeology)
  • Selectivity
  • Combinatorial chemistry
  • Stereochemistry
UN Sustainable Development Goals
  • Affordable and clean energy
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