ArticleACS catalysis2022
Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles.
Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Formal Hydride Abstraction: A Unified Photoredox Platform for Nucleophilic C(sp3)-H Functionalization.Accounts of chemical research · 2026Article
- A radical-polar crossover approach to complex nitrogen heterocycles via the triplet state.Chem · 2026Article
- Triazenyl Furans as Diels-Alder Dienes.Journal of the American Chemical Society · 2026Article
- Recent Advances in Intramolecular C─N Bond Formation for Pyrrolidine Synthesis.ChemistryOpen · 2026Review
- Organophotoredox Dioxygenation of Alkenes via ROH···F-ActivatedOrganic letters · 2025Article
- Photocatalysis Enables Chemodivergent Radical Polar Crossover: Ritter-Type Amidation vs Heck-Type Olefin Carbofunctionalizations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- 1,3-Difunctionalization of [1.1.1]propellane through iron-hydride catalyzed hydropyridylation.Nature communications · 2024Article
- Synthesis of constrained bicycloalkanes through bibase-promoted brook rearrangement/radical-polar crossover cyclization.Chemical science · 2024Article
- Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines.Journal of the American Chemical Society · 2024Article
- Mechanisms for radical reactions initiating fromBeilstein journal of organic chemistry · 2024Article
- Synthesis of tertiary alkylphosphonate oligonucleotides through light-driven radical-polar crossover reactions.Nature communications · 2023Article
- Visible-light-mediated synthesis of oxime estersRSC advances · 2023Article
- Tunable [3+2] and [4+2] annulations for pyrrolidine and piperidine synthesis.Chemical communications (Cambridge, England) · 2023Article
- Recent advancements in iodide/phosphine-mediated photoredox radical reactions.Beilstein journal of organic chemistry · 2023Review
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Authors and funding
6 authors.
Funding
Abstract
We introduce here a two-component annulation strategy that provides access to a diverse collection of five- and six-membered saturated heterocycles from aryl alkenes and a family of redox-active radical precursors bearing tethered nucleophiles. This transformation is mediated by a combination of an Ir(III) photocatalyst and a Brønsted acid under visible-light irradiation. A reductive proton-coupled electron transfer generates a reactive radical which undergoes addition to an alkene. Then, an oxidative radical-polar crossover step leading to carbocation formation is followed by ring closure through cyclization of the tethered nucleophile. A wide range of heterocycles are easily accessible, including pyrrolidines, piperidines, tetrahydrofurans, morpholines, δ-valerolactones, and dioxanones. We demonstrate the scope of this approach through broad structural variation of both reaction components. This method is amenable to gram-scale preparation and to complex fragment coupling.
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