ArticleJournal of the American Chemical Society2014
Metalloradical approach to 2H-chromenes.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed.
- Light Induced Cobalt(III) Carbene Radical Formation from Dimethyl Malonate As Carbene Precursor.Organometallics · 2024Article
- Metalloradical Catalysis: General Approach for Controlling Reactivity and Selectivity of Homolytic Radical Reactions.Angewandte Chemie (International ed. in English) · 2024Review
- Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.Chemical reviews · 2022Review
- Metalloradical Activation of In Situ-Generated α-Alkynyldiazomethanes for Asymmetric Radical Cyclopropanation of Alkenes.Journal of the American Chemical Society · 2022Article
- Catalytic Synthesis of 1Journal of the American Chemical Society · 2021Article
- Controlling Radical-Type Single-Electron Elementary Steps in Catalysis with Redox-Active Ligands and Substrates.JACS Au · 2021Review
- Asymmetric Radical Process for General Synthesis of Chiral Heteroaryl Cyclopropanes.Journal of the American Chemical Society · 2021Article
- Controlling Enantioselectivity and Diastereoselectivity in Radical Cascade Cyclization for Construction of Bicyclic Structures.Journal of the American Chemical Society · 2021Article
- [2 + 2 + 1] Cycloaddition ofChemical science · 2021Article
- Revisiting the Electronic Structure of Cobalt Porphyrin Nitrene and Carbene Radicals with NEVPT2-CASSCF Calculations: Doublet versus Quartet Ground States.Inorganic chemistry · 2021Article
- Co-Catalyzed Transannulation of Pyridotriazoles with Isothiocyanates and Xanthate Esters.Organic letters · 2020Article
- Catalytic Synthesis of 8-Membered Ring Compounds via Cobalt(III)-Carbene Radicals.Angewandte Chemie (International ed. in English) · 2020Article
- A Carbene-Extended ATRA Reaction.Angewandte Chemie (International ed. in English) · 2019Article
- Enantioselective Radical Construction of 5-Membered Cyclic Sulfonamides by Metalloradical C-H Amination.Journal of the American Chemical Society · 2019Article
- Bis(imino)pyridine iron complexes for catalytic carbene transfer reactions.Chemical science · 2019Article
- [Co(TPP)]-Catalyzed Formation of Substituted Piperidines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Radical-Type Reactivity and Catalysis by Single-Electron Transfer to or from Redox-Active Ligands.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(spChemical science · 2018Article
- Iodine-catalyzed diazo activation to access radical reactivity.Nature communications · 2018Article
- Catalytic Synthesis of Indolines by Hydrogen Atom Transfer to Cobalt(III)-Carbene Radicals.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
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6 authors.
Funding
Abstract
Cobalt(III)-carbene radicals, generated through metalloradical activation of salicyl N-tosylhydrazones by cobalt(II) complexes of porphyrins, readily undergo radical addition to terminal alkynes to produce salicyl-vinyl radical intermediates. Subsequent hydrogen atom transfer (HAT) from the hydroxy group of the salicyl moiety to the vinyl radical leads to the formation of 2H-chromenes. The Co(II)-catalyzed process can tolerate various substitution patterns and produces the corresponding 2H-chromene products in good isolated yields. EPR spectroscopy and radical-trapping experiments with TEMPO are in agreement with the proposed radical mechanism. DFT calculations reveal the formation of the salicyl-vinyl radical intermediate by a metalloradical-mediated process. Unexpectedly, subsequent HAT from the hydroxy moiety to the vinyl radical leads to formation of an o-quinone methide intermediate, which dissociates spontaneously from the cobalt center and easily undergoes an endocyclic, sigmatropic ring-closing reaction to form the final 2H-chromene product.
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