ArticleJournal of the American Chemical Society2021
Direct Deamination of Primary Amines via Isodiazene Intermediates.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 26 papers.
What it found
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Who cites it
26 citing papers in PubMed.
- Alkyl-to-Alkyl Palladium Migration Enables Remote C-C Bond Formation.Journal of the American Chemical Society · 2026Article
- Direct Deaminative Alkynylation of Aliphatic Primary Amines.Angewandte Chemie (International ed. in English) · 2026Article
- Anomeric Amides: Valuable Reagents in Synthetic Organic Chemistry.Angewandte Chemie (International ed. in English) · 2026Review
- Larger Substituents Enhance Stereospecificity in 1,1-Diazene Nitrogen Extrusion through Attenuation of Dynamic Mismatching.JACS Au · 2026Article
- Decoding the Nested, Multicycle Mechanism of Ni-Catalyzed Redox-Neutral Cross-Coupling through Temperature Scanning Reaction Calorimetry.Journal of the American Chemical Society · 2026Article
- Article
- Facile and Practical Synthesis of Substituted Piperidine-2,6-Diones Under Transition-Metal Free Condition.ChemistryOpen · 2025Article
- Deaminative Giese-type reaction.Nature chemistry · 2025Article
- Accessing sulfonamides via formal SONature chemistry · 2025Article
- Catalytic diazene synthesis from sterically hindered amines for deaminative functionalization.Nature communications · 2025Article
- Article
- Nitrene-mediated aminative N-N-N coupling: facile access to triazene 1-oxides.Chemical science · 2025Article
- Redox-Tunable Ring Expansion Enabled By A Single-Component Electrophilic Nitrogen Atom Synthon.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of Substituted Tetralins via Nitrogen Deletion/Diels-Alder Cascade Reaction.The Journal of organic chemistry · 2024Article
- Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.Dalton transactions (Cambridge, England : 2003) · 2024Review
- Hydro- and deutero-deamination of primary amines using O-diphenylphosphinylhydroxylamine.Nature communications · 2024Article
- Mechanochemical Synthesis of a Sodium Anion Complex [NaInorganic chemistry · 2024Article
- Facile and efficient transformation of thiols to disulfidesRSC advances · 2024Article
- Influence of Cage Effects in Directing the Outcome of C-X Bond Forming Reactions.ACS organic & inorganic Au · 2024Review
- Synthesis of dienes from pyrrolidines using skeletal modification.Nature communications · 2023Article
Corrections and comments
- Erratum issued
Authors and funding
6 authors.
Funding
Abstract
We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.
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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.