ArticleAngewandte Chemie (International ed. in English)2019
Oxidative Amide Coupling from Functionally Diverse Alcohols and Amines Using Aerobic Copper/Nitroxyl Catalysis.
Article in Angewandte Chemie (International ed. in English), 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, 36 citations in OpenAlex.
- Skeletal Editing of Alkenes with Nitroarenes via Photoinduced Rearrangement of N─O═C Dipoles Forms Lactams and Amides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Copper-Nitroxyl-Catalyzed α-Oxygenation of Cyclic Secondary Amines Including Application to Late-Stage Functionalization.Journal of the American Chemical Society · 2024Article
- Progress in C-C and C-Heteroatom Bonds Construction Using Alcohols as Acyl Precursors.Molecules (Basel, Switzerland) · 2022Review
- Redox-active molecules as organocatalysts for selective oxidative transformations - an unperceived organocatalysis field.Beilstein journal of organic chemistry · 2022Article
- A cobalt adduct of an N-hydroxy-piperidinium cation.Journal of coordination chemistry · 2022Article
- Efficient Aerobic Oxidation of Organic Molecules by Multistep Electron Transfer.Angewandte Chemie (International ed. in English) · 2021Review
- Near-Ambient-Temperature Dehydrogenative Synthesis of the Amide Bond: Mechanistic Insight and Applications.ACS catalysis · 2021Article
- C(spScience (New York, N.Y.) · 2021Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The aerobic Cu/ABNO catalyzed oxidative coupling of alcohols and amines is highlighted in the synthesis of amide bonds in diverse drug-like molecules (ABNO=9-azabicyclo[3.3.1]nonane N-oxyl). The robust method leverages the privileged reactivity of alcohols bearing electronegative hetero- atoms (O, F, N, Cl) in the β-position. The reaction tolerates over 20 unique functional groups and is demonstrated on a 15 mmol scale under air. Steric constraints of the catalyst allow for chemoselective amidation of primary amines in the presence of secondary amines. All catalyst components are commercially available, and the reaction proceeds under mild conditions with retention of stereocenters in both reaction partners, while producing only water as a by-product.
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Registered trials
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.