ArticleAngewandte Chemie (International ed. in English)2021
Photochemical Carbene Transfer Reactions of Aryl/Aryl Diazoalkanes-Experiment and Theory*.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 104 citations in OpenAlex.
- Carbene-Ketene Formal [3 + 2] Cycloaddition Enabled by Visible-Light-Induced Dual Photolysis of Diazo Compounds.JACS Au · 2026Article
- Tunable Skeletal Editing of Benzothiazole and Benzisothiazole Via Carbene Transfer Reactions.JACS Au · 2025Article
- The Genuine Carbene Conundrum.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Facile Access to Hindered Ethers via Photoinduced O-H Bond Insertions.ACS central science · 2025Article
- Photoinduced C-Cl Bond Activation of Polychloroalkanes with Triplet Carbenes: Synthetic Applications and Mechanistic Studies.JACS Au · 2025Article
- Unique Reactivity of Triazolyl Diazoacetates under Photochemical Conditions.ACS organic & inorganic Au · 2024Article
- Visible Light-Induced Reactions of Diazo Compounds and Their Precursors.Chemical reviews · 2024Review
- Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates.JACS Au · 2024Article
- Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of spChemical science · 2023Article
- Unveiling catalyst-free electro-photochemical reactivity of aryl diazoesters and facile synthesis of oxazoles, imide-fused pyrroles and tetrahydro-epoxy-pyridinesChemical science · 2023Article
- Electrochemical oxidative difunctionalization of diazo compounds with two different nucleophiles.Nature communications · 2023Article
- Visible-light-induced organocatalytic enantioselective N-H insertion of α-diazoesters enabled by indirect free carbene capture.Chemical science · 2023Article
- Photo-Induced Homologation of Carbonyl Compounds for Iterative Syntheses.Angewandte Chemie (International ed. in English) · 2022Article
- Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines.ACS omega · 2022Article
- Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Photocatalytic gem-Difluoroolefination Reactions by a Formal C-C Coupling/Defluorination Reaction with Diazoacetates.Angewandte Chemie (International ed. in English) · 2022Article
- A DFT Study on the Molecular Mechanism of Additions of Electrophilic and Nucleophilic Carbenes to Non-Enolizable Cycloaliphatic Thioketones.Molecules (Basel, Switzerland) · 2021Article
- Photochemical Carbene Transfer Reactions of Aryl/Aryl Diazoalkanes-Experiment and Theory*.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Controlling the reactivity of carbene intermediates is a key parameter in the development of selective carbene transfer reactions and is usually achieved by metal complexes via singlet metal-carbene intermediates. In this combined experimental and computational studies, we show that the reactivity of free diaryl carbenes can be controlled by the electronic properties of the substituents without the need of external additives. The introduction of electron-donating and -withdrawing groups results in a significant perturbation of singlet triplet energy splitting of the diaryl carbene intermediate and of activation energies of consecutive carbene transfer reactions. This strategy now overcomes a long-standing paradigm in the reactivity of diaryl carbenes and allows the realization of highly chemoselective carbene transfer reactions with alkynes. We could show that free diaryl carbenes can be readily accessed via photolysis of the corresponding diazo compounds and that these carbenes can undergo highly chemoselective cyclopropenation, cascade, or C-H functionalization reactions. Experimental and theoretical mechanistic analyses confirm the participation of different carbene spin states and rationalize for the observed reactivity.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.