ArticleJournal of the American Chemical Society2013
Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Synthesis of chiral lactams by asymmetric nitrogen insertion.Chemical science · 2026Article
- 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
- Computational Study of a Copper-Catalyzed Synthesis of Fluoroalcohols from Alkylboranes and Ketones.The Journal of organic chemistry · 2025Article
- Hydrogen Bonding and Vaporization Thermodynamics in Hexafluoroisopropanol-Acetone and -Methanol Mixtures. A Joined Cluster Analysis and Molecular Dynamic Study.Chemphyschem : a European journal of chemical physics and physical chemistry · 2022Article
- Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.Topics in current chemistry (Cham) · 2021Review
- Pd-catalyzed stereoselective tandem ring-opening amination/cyclization of vinyl γ-lactones: access to caprolactam diversity.Chemical science · 2020Article
- Hexafluoroisopropanol-Promoted Disulfidation and Diselenation of Alkyne, Alkene, and Allene.Organic letters · 2020Article
- Intramolecular CspChemical science · 2020Article
- Allylic azides: synthesis, reactivity, and the Winstein rearrangement.Organic & biomolecular chemistry · 2019Review
- Reagent-controlled regiodivergent ring expansions of steroids.Nature communications · 2018Article
- Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol.Molecules (Basel, Switzerland) · 2015Article
- Temperature dependence of turnover in a Sc(OTf)Tetrahedron letters · 2015Article
- Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction.Beilstein journal of organic chemistry · 2015Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.
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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.