ArticleChem catalysis2023
Photochemical iron-catalyzed decarboxylative azidation via the merger of ligand-to-metal charge transfer and radical ligand transfer catalysis.
Article in Chem catalysis, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed.
- Light-Driven Iron-Mediated Thiotrifluoromethylation of Alkenes Using CFOrganic letters · 2026Article
- Acridinium amidate as a hydrogen-bonding photocatalyst for direct decarboxylative alkylation of native carboxylic acids.Chemical science · 2026Article
- Photocatalysts for the decarboxylation conversion of C(spRSC advances · 2026Review
- Base Metal Photocatalysts: A Bright Future in Photoredox Catalysis?Organometallics · 2026Article
- Ligand-Enabled Photocatalytic Reactivity of Iron(III) Halide Salts with Cyan and Green Light.Organic letters · 2026Article
- Accessing Molecular Complexity from Methane and Other Gaseous Alkanes via Photocatalytic Cascade Cyclization.Angewandte Chemie (International ed. in English) · 2026Article
- Carbon-Heteroatom Bond Formation via Photoinduced Decarboxylative Radical Coupling Reactions.ACS omega · 2025Review
- Bimolecular Homolytic Substitution (SACS central science · 2025Review
- LMCT-Driven Iron Photocatalysis: Mechanistic Insights and Synthetic Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Iron-Catalyzed Decarboxylative Sulfinylation of Alkyl Carboxylic Acids.Organic letters · 2025Article
- Overcoming Challenges in Small-Ring Transfer: Direct Decarboxylative Hydroalkylation of Alkenes via Iron-Thiol Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Unlocking Chromium Decarboxylative Ligand-to-Metal Charge Transfer: Efficient and Redox-Neutral Allylation of Aldehydes Using Carboxylic Acids.Journal of the American Chemical Society · 2025Article
- Molecular Design Principles for Photoactive Transition Metal Complexes: A Guide for "Photo-Motivated" Chemists.Journal of the American Chemical Society · 2025Review
- Anti-Markovnikov hydro- and deuterochlorination of unsaturated hydrocarbons using iron photocatalysis.Nature synthesis · 2025Article
- Modular access to saturated bioisosteres of anilines via photoelectrochemical decarboxylative C(spNature communications · 2025Article
- Merging photoredox with metalloenzymatic catalysis for enantioselective decarboxylative C(spNature catalysis · 2024Article
- Decarboxylative Cross-Coupling Enabled by Fe and Ni Metallaphotoredox Catalysis.Journal of the American Chemical Society · 2024Article
- Building Catalytic Reactions One Electron at a Time.Accounts of chemical research · 2024Article
- Mechanochemistry Drives Alkene Difunctionalization via Radical Ligand Transfer and Electron Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Iron photocatalysis via Brønsted acid-unlocked ligand-to-metal charge transfer.Nature communications · 2024Article
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Authors and funding
6 authors.
Funding
Abstract
Ligand-to-metal charge transfer (LMCT) using stoichiometric copper salts has recently been shown to permit decarboxylative C-N bond formation via an LMCT/radical polar crossover (RPC) mechanism; however, this method is unable to function catalytically and cannot successfully engage unactivated alkyl carboxylic acids, presenting challenges to the general applicability of this approach. Leveraging the concepts of ligand-to-metal charge transfer (LMCT) and radical-ligand-transfer (RLT), we herein report the first photochemical, iron-catalyzed direct decarboxylative azidation. Simply irradiating an inexpensive iron nitrate catalyst in the presence of azidotrimethylsilane allows for a diverse array of carboxylic acids to be converted to corresponding organic azides directly with broad functional group tolerance and mild conditions. Intriguingly, no additional external oxidant is required for this reaction to proceed, simplifying the reaction protocol. Finally, mechanistic studies are consistent with a radical mechanism and suggest that the nitrate counteranion serves as an internal oxidant for turnover of the iron catalyst.
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