ArticleChemistry (Weinheim an der Bergstrasse, Germany)2019
Uncatalyzed Oxidative C-H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 21 citations in OpenAlex.
- C-H amination chemistry mediated by trinuclear Cu(I) sites supported by a ligand scaffold featuring an arene platform and tetramethylguanidinyl residues.Dalton transactions (Cambridge, England : 2003) · 2024Article
- A Comparative Study of Cationic Copper(I) Reagents Supported by Bipodal Tetramethylguanidinyl-Containing Ligands as Nitrene-Transfer Catalysts.ACS omega · 2024Article
- Nitrene-Transfer Chemistry to C-H and C═C Bonds Mediated by Triangular Coinage Metal Platforms Supported by Triply Bridging Pnictogen Elements Sb(III) and Bi(III).Organometallics · 2024Article
- Site selective gold(i)-catalysed benzylic C-H aminationChemical science · 2023Article
- Evaluation of the Synthetic Scope and the Reaction Pathways of Proton-Coupled Electron Transfer with Redox-Active Guanidines in C-H Activation Processes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Electronically Asynchronous Transition States for C-N Bond Formation by ElectrophilicACS catalysis · 2020Article
- Intramolecular CspChemical science · 2020Article
- Uncatalyzed Oxidative C-H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
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4 authors at 1 institution in 1 country.
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Abstract
A new method for the one-step C-H amination of xanthene and thioxanthene with sulfonamides is reported, without the need for any metal catalyst. A benzoquinone was employed as a hydride (or two-electron and one-proton) acceptor. Moreover, a previously unknown and uncatalyzed reaction between iminoiodanes and xanthene, thioxanthene and dihydroacridines (9,10-dihydro-9-heteroanthracenes or dihydroheteroanthracenes) is disclosed. The reactions proceed through hydride transfer from the heteroarene substrate to the iminoiodane or benzoquinone, followed by conjugate addition of the sulfonamide to the oxidized heteroaromatic compounds. These findings may have important mechanistic implications for metal-catalyzed C-H amination processes involving nitrene transfer from iminoiodanes to dihydroheteroanthracenes. Due to the weak C-H bond, xanthene is an often-employed substrate in mechanistic studies of C-H amination reactions, which are generally proposed to proceed via metal-catalyzed nitrene insertion, especially for reactions involving nitrene or imido complexes that are less reactive (i.e., less strongly oxidizing). However, these substrates clearly undergo non-catalyzed (proton-coupled) redox coupling with amines, thus providing alternative pathways to the widely assumed metal-catalyzed pathways.
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