ArticleJournal of the American Chemical Society2019
Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- From reagents to feedstocks: reprogramming heteroatom-containing molecules in modern organic synthesis.Molecular diversity · 2026Review
- α-Amido Sulfonium Salts Provide a Platform for Photocatalytic Metal-Free Carbon-Carbon Bond Formation in Amides.ACS catalysis · 2025Article
- Inverse conjugate additions of acrylic amides and esters with F/Cl/O/N-nucleophiles and CFScience advances · 2025Article
- Catalytic Enantioselective Synthesis of 1,4-(Hetero) Dicarbonyl Compounds through α-Carbonyl Umpolung.Journal of the American Chemical Society · 2025Article
- Article
- Recent Advances in C-H Functionalisation through Indirect Hydrogen Atom Transfer.Molecules (Basel, Switzerland) · 2023Review
- Article
- Nms-Amides: An Amine Protecting Group with Unique Stability and Selectivity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- New Strategies for the Functionalization of Carbonyl Derivatives via α-Umpolung: From Enolates to Enolonium Ions.Accounts of chemical research · 2023Article
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (International ed. in English) · 2022Review
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Review
- An Expedient Method for the Umpolung Coupling of Enols with Heteronucleophiles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Sulfur(iv)-mediated umpolung α-heterofunctionalization of 2-oxazolines.Chemical science · 2022Article
- Uniting Amide Synthesis and Activation by PJournal of the American Chemical Society · 2021Article
- Chemoselektive γ-Oxidation von β,γ-ungesättigten Amiden mit TEMPO.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Article
- Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO.Angewandte Chemie (International ed. in English) · 2021Article
- Direct Synthesis of Enamides via Electrophilic Activation of Amides.Journal of the American Chemical Society · 2021Article
- Chiral Hypervalent Iodine Catalysis Enables an Unusual Regiodivergent Intermolecular Olefin Aminooxygenation.JACS Au · 2021Article
- Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents.Organic letters · 2020Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Functionalization at the α-position of carbonyl compounds has classically relied on enolate chemistry. As a result, the generation of a new C-X bond, where X is more electronegative than carbon requires an oxidation event. Herein we show that, by rendering the α-position of amides electrophilic through a mild and chemoselective umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur, and halogen nucleophiles can be used to generate α-functionalized amides. More than 60 examples are presented to establish the generality of this process, and calculations of the mechanistic aspects underline a fragmentation pathway that accounts for the broadness of this methodology.
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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.