ArticleNature communications2022
Rapid access to polycyclic N-heteroarenes from unactivated, simple azines via a base-promoted Minisci-type annulation.
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 4 papers.
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Who cites it
4 citing papers in PubMed.
- Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.Chemical reviews · 2025Review
- Light-assisted functionalization of aryl radicals towards metal-free cross-coupling.Nature reviews. Chemistry · 2025Review
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Cyclic Homo- and Heterohalogen Di-λJournal of the American Chemical Society · 2023Article
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Authors and funding
14 authors.
Funding
Abstract
Conventional synthetic methods to yield polycyclic heteroarenes have largely relied on metal-mediated arylation reactions requiring pre-functionalised substrates. However, the functionalisation of unactivated azines has been restricted because of their intrinsic low reactivity. Herein, we report a transition-metal-free, radical relay π-extension approach to produce N-doped polycyclic aromatic compounds directly from simple azines and cyclic iodonium salts. Mechanistic and electron paramagnetic resonance studies provide evidence for the in situ generation of organic electron donors, while chemical trapping and electrochemical experiments implicate an iodanyl radical intermediate serving as a formal biaryl radical equivalent. This intermediate, formed by one-electron reduction of the cyclic iodonium salt, acts as the key intermediate driving the Minisci-type arylation reaction. The synthetic utility of this radical-based annulative π-extension method is highlighted by the preparation of an N-doped heptacyclic nanographene fragment through fourfold C-H arylation.
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Registered trials
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