ArticleChemistry (Weinheim an der Bergstrasse, Germany)2018
Catalytic Synthesis of Indolines by Hydrogen Atom Transfer to Cobalt(III)-Carbene Radicals.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 62 citations in OpenAlex.
- Enantioselective Intramolecular C-H Alkylation Catalyzed by a Nonsymmetric Chiral Cobalt Porphyrin.Journal of the American Chemical Society · 2026Article
- Intramolecular Cobalt Porphyrin-Catalyzed Alkylation of 1-Isoindolinones by Site-Selective Insertion into a C(spOrganic letters · 2024Article
- Metalloradical Catalysis: General Approach for Controlling Reactivity and Selectivity of Homolytic Radical Reactions.Angewandte Chemie (International ed. in English) · 2024Review
- Carbene Radicals in Transition-Metal-Catalyzed Reactions.ACS catalysis · 2023Review
- Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.Chemical reviews · 2022Review
- 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 Synthesis of 2-Arylindolines and 2,2-Disubstituted Indolines by Kinetic Resolution.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Revisiting the Electronic Structure of Cobalt Porphyrin Nitrene and Carbene Radicals with NEVPT2-CASSCF Calculations: Doublet versus Quartet Ground States.Inorganic chemistry · 2021Article
- Titanocene-Catalyzed [2+2] Cycloaddition of Bisenones and Comparison with Photoredox Catalysis and Established Methods.Angewandte Chemie (International ed. in English) · 2021Article
- Transition Metal Catalyzed Insertion Reactions with Donor/Donor Carbenes.Angewandte Chemie (International ed. in English) · 2021Review
- Enantioconvergent Amination of Racemic Tertiary C-H Bonds.Journal of the American Chemical Society · 2020Article
- 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
- Enantioselective Radical Construction of 5-Membered Cyclic Sulfonamides by Metalloradical C-H Amination.Journal of the American Chemical Society · 2019Article
- Merging Regiodivergent Catalysis with Atom-Economical Radical Arylation.Angewandte Chemie (International ed. in English) · 2019Article
- Efficient Copper-Catalyzed Multicomponent Synthesis ofJournal of the American Chemical Society · 2019Article
- [Co(TPP)]-Catalyzed Formation of Substituted Piperidines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Next-Generation DAngewandte Chemie (International ed. in English) · 2019Article
- Catalytic Radical Process for Enantioselective Amination of C(spAngewandte Chemie (International ed. in English) · 2018Article
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3 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report a new method for the synthesis of indolines from o-aminobenzylidine N-tosylhydrazones proceeding through a cobalt(III)-carbene radical intermediate. This methodology employs the use of inexpensive commercially available reagents and allows for the transformation of easily derivatized benzaldehyde-derived precursors to functionalized indoline products. This transformation takes advantage of the known propensity of radicals to undergo rapid intramolecular 1,5-hydrogen atom transfer (1,5-HAT) to form more stabilized radical intermediates. Computational investigations using density functional theory identify remarkably low barriers for 1,5-HAT and subsequent radical rebound displacement, providing support for the proposed mechanism. We explore the effect of a variety of nitrogen substituents, and highlight the importance of adequate resonance stabilization of radical intermediates to the success of the transformation. Furthermore, we evaluate the steric and electronic effects of substituents on the aniline ring. This transformation is the first reported example of the synthesis of nitrogen-containing heterocycles from cobalt(III)-carbene radical precursors.
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