ArticleJournal of the American Chemical Society2023
1,2-Redox Transpositions of Tertiary Amides.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 24 citations in OpenAlex.
- Lactam Framework Editing via Formal Methylene Deletion.Journal of the American Chemical Society · 2026Article
- Ketone displacement and migration enabled by trifunctionalization of vinyl triflates.Nature communications · 2026Article
- Nickel-Catalyzed cine-Substitution Toward Carbonyl Dance.Chemistry, an Asian journal · 2026Article
- 1,2-Oxygen Transposition on Arenes Enabled by Palladium/Norbornene Cooperative Catalysis.Journal of the American Chemical Society · 2025Article
- Iridium-Catalyzed Reductive Deoxygenation of Esters for the Synthesis of Sterically Hindered Ethers.Angewandte Chemie (International ed. in English) · 2025Article
- Oxygen transposition of formamide to α-aminoketone moiety in a carbene-initiated domino reaction.Nature chemistry · 2025Article
- Regioselective Synthesis of β,γ-Unsaturated Amides from Unactivated Alkenes.The Journal of organic chemistry · 2025Article
- Merging SOMO activation with transition metal catalysis: Deoxygenative functionalization of amides to β-aryl amines.Science advances · 2025Article
- α,β-Desaturation and Formal β-C(spJournal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Reactions capable of transposing the oxidation levels of adjacent carbon atoms enable rapid and fundamental alteration of a molecule's reactivity. Herein, we report the 1,2-transposition of the carbon atom oxidation level in cyclic and acyclic tertiary amides, resulting in the one-pot synthesis of 1,2- and 1,3-oxygenated tertiary amines. This oxidation level transfer was facilitated by the careful orchestration of an iridium-catalyzed reduction with the functionalization of transiently formed enamine intermediates. A novel 1,2-carbonyl transposition is described, and the breadth of this redox transposition strategy has been further explored by the development of aminoalcohol and enaminone syntheses. The diverse β-functionalized amine products were shown to be multifaceted and valuable synthetic intermediates, accessing challenging biologically relevant motifs.
Identifiers
What OpenQuestion holds
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.