ArticleJournal of the American Chemical Society2017
Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 60 papers.
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Who cites it
60 citing papers in PubMed.
- Photochemical, electrochemical and electrophotochemical C-N bond-forming cross-coupling reactions.Nature reviews. Chemistry · 2026Review
- Enantioconvergent benzylic C(spScience (New York, N.Y.) · 2025Article
- Aryl Acid-Alcohol Cross-Coupling: C(spJournal of the American Chemical Society · 2025Article
- Visible-Light-Mediated Rose Bengal- or [Ru(bpy)ACS omega · 2025Article
- Photoinduced Pd-Catalyzed Direct Sulfonylation of Allylic C-H Bonds.Angewandte Chemie (International ed. in English) · 2025Article
- Photo-induced decarboxylative C-S bond formation to access sterically hindered unsymmetric S-alkyl thiosulfonates and SS-alkyl thiosulfonates.Nature communications · 2024Article
- Direct catalytic photodecarboxylative amination of carboxylic acids with diazirines for divergent access to nitrogen-containing compounds.Cell reports. Physical science · 2024Article
- Decarboxylative stereoretentive C-N coupling by harnessing aminating reagent.Nature communications · 2024Article
- Mechanisms for radical reactions initiating fromBeilstein journal of organic chemistry · 2024Article
- A Chemoselective Polarity-Mismatched Photocatalytic C(spAngewandte Chemie (International ed. in English) · 2023Article
- Decarboxylation of β-boryl NHPI esters enables radical 1,2-boron shift for the assembly of versatile organoborons.Nature communications · 2023Article
- Aminodealkenylation: Ozonolysis and copper catalysis convert C(spScience (New York, N.Y.) · 2023Article
- Bismuth radical catalysis in the activation and coupling of redox-active electrophiles.Nature chemistry · 2023Article
- Article
- General access to cubanes as benzene bioisosteres.Nature · 2023Article
- Radical Decarboxylative Carbon-Nitrogen Bond Formation.Molecules (Basel, Switzerland) · 2023Review
- Azolation of Benzylic C-H Bonds via Photoredox-Catalyzed Carbocation Generation.Journal of the American Chemical Society · 2023Article
- Synthesis of Ketonylated Carbocycles via Excited-State Copper-Catalyzed Radical Carbo-Aroylation of Unactivated Alkenes.ChemCatChem · 2023Article
- Properties of Amine-Containing Ligands That Are Necessary for Visible-Light-Promoted Catalysis with Divalent Europium.Inorganic chemistry · 2022Article
- Excited-State Copper-Catalyzed [4 + 1] Annulation Reaction Enables Modular Synthesis of α,β-Unsaturated-γ-Lactams.Journal of the American Chemical Society · 2022Article
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4 authors.
Funding
Abstract
The Curtius rearrangement is a classic, powerful method for converting carboxylic acids into protected amines, but its widespread use is impeded by safety issues (the need to handle azides). We have developed an alternative to the Curtius rearrangement that employs a copper catalyst in combination with blue-LED irradiation to achieve the decarboxylative coupling of aliphatic carboxylic acid derivatives (specifically, readily available N-hydroxyphthalimide esters) to afford protected amines under mild conditions. This C-N bond-forming process is compatible with a wide array of functional groups, including an alcohol, aldehyde, epoxide, indole, nitroalkane, and sulfide. Control reactions and mechanistic studies are consistent with the hypothesis that copper species are engaged in both the photochemistry and the key bond-forming step, which occurs through out-of-cage coupling of an alkyl radical.
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