ArticleNature communications2022
Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Photoinduced Hydrogenative Dearomatization With Homocoupling of Quinolines to Construct Octahydro-4,4'-biquinolines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Article
- Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.Accounts of chemical research · 2025Article
- Reaction strategies for the meta-selective functionalization of pyridine through dearomatization.Molecular diversity · 2025Review
- Single-Atom Co-NJACS Au · 2024Article
- Photochemical dearomative skeletal modifications of heteroaromatics.Chemical Society reviews · 2024Review
- Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines.Chemical reviews · 2024Review
- Combining photoredox catalysis and hydrogen atom transfer for dearomative functionalization of electron rich heteroarenes.Chemical science · 2023Article
- Uncanonical Semireduction of Quinolines and Isoquinolines via Regioselective HAT-Promoted Hydrosilylation.Journal of the American Chemical Society · 2023Article
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Authors and funding
8 authors.
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Abstract
Reactions that lead to destruction of aromatic ring systems often require harsh conditions and, thus, take place with poor selectivities. Selective partial dearomatization of fused arenes is even more challenging but can be a strategic approach to creating versatile, complex polycyclic frameworks. Herein we describe a general organophotoredox approach for the chemo- and regioselective dearomatization of structurally diverse polycyclic aromatics, including quinolines, isoquinolines, quinoxalines, naphthalenes, anthracenes and phenanthrenes. The success of the method for chemoselective oxidative rupture of aromatic moieties relies on precise manipulation of the electronic nature of the fused polycyclic arenes. Mechanistic studies show that the addition of a hydrogen atom transfer (HAT) agent helps favor the dearomatization pathway over the more thermodynamically downhill aromatization pathway. We show that this strategy can be applied to rapid synthesis of biologically valued targets and late-stage skeletal remodeling en route to complex structures.
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