ArticleMolecules (Basel, Switzerland)2024
Visible-Light-Promoted Tandem Skeletal Rearrangement/Dearomatization of Heteroaryl Enallenes.
Article in Molecules (Basel, Switzerland), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 6 citations in OpenAlex.
- Visible-Light Mediated Activation of 1,3-Dienes and Allenes via Energy Transfers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Light-Mediated Binaphthyl Enhanced [2 + 2] Dearomatization of Heterocycles via an Energy-Transfer Process.Organic letters · 2025Article
- Oxidative Scission of Bicyclo[2.2.2]octenones: Untying the α-Dimethoxycarbonyl.The Journal of organic chemistry · 2025Article
- The effect of tethered bi-naphthyls on visible-light promoted alkene-alkene [2 + 2] cycloadditions.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2024Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
Access to complex three-dimensional molecular architectures via dearomatization of ubiquitous aryl rings is a powerful synthetic tool, which faces, however, an inherent challenge to overcome energetic costs due to the loss of aromatic stabilization energy. Photochemical methods that allow one to populate high-energy states can thus be an ideal strategy to accomplish otherwise prohibitive reaction pathways. We present an original dearomative rearrangement of heteroaryl acryloylallenamides that leads to complex fused tricycles. The visible-light-promoted method occurs under mild conditions and tolerates a variety of functional groups. According to DFT modeling used to rationalize the outcome of the cascade, the reaction involves a sequential [2+2] allene-alkene photocycloaddition, which is followed by a selective retro- [2+2] step that paves the way for the dearomatization of the heteroaryl partner. This scenario is original with respect to the reported photochemical reactivity of similar substrates and thus holds promise for ample future developments.
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Registered trials
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