ArticleJournal of the American Chemical Society2011
From bifunctional to trifunctional (tricomponent nucleophile-transition metal-lewis acid) catalysis: the catalytic, enantioselective α-fluorination of acid chlorides.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 90 citations in OpenAlex.
- Enantioselective isothiourea-catalysed α-fluorination of C1-ammonium enolates generated from arylesters.Journal of fluorine chemistry · 2025Article
- Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates.Tetrahedron chem · 2024Article
- Photochemical Wolff Rearrangement Initiated Generation and Subsequent α-Chlorination of C1 Ammonium Enolates.Organic letters · 2023Article
- Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions.Organic letters · 2021Article
- Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles.Angewandte Chemie (International ed. in English) · 2018Article
- Ketones as directing groups in photocatalytic spChemical science · 2017Article
- Forging Fluorine-Containing Quaternary Stereocenters by a Light-Driven Organocatalytic Aldol Desymmetrization Process.Angewandte Chemie (International ed. in English) · 2017Article
- Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions.Chemical reviews · 2015Review
- Enantioselective nucleophile-catalyzed synthesis of tertiary alkyl fluorides via the α-fluorination of ketenes: synthetic and mechanistic studies.Journal of the American Chemical Society · 2014Article
- Asymmetric fluorination of α-branched cyclohexanones enabled by a combination of chiral anion phase-transfer catalysis and enamine catalysis using protected amino acids.Journal of the American Chemical Society · 2014Article
- Palladium and organocatalysis: an excellent recipe for asymmetric synthesis.Molecules (Basel, Switzerland) · 2013Review
- Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals.Chemical science · 2013Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
We report in full detail our studies on the catalytic, asymmetric α-fluorination of acid chlorides, a practical method that produces an array of α-fluorocarboxylic acid derivatives in which improved yield and virtually complete enantioselectivity are controlled through electrophilic fluorination of a ketene enolate intermediate. We discovered, for the first time, that a third catalyst, a Lewis acidic lithium salt, could be introduced into a dually activated system to amplify yields of aliphatic products, primarily through activation of the fluorinating agent. Through our mechanistic studies (based on kinetic data, isotopic labeling, spectroscopic measurements, and theoretical calculations) we were able to utilize our understanding of this "trifunctional" reaction to optimize the conditions and obtain new products in good yield and excellent enantioselectivity.
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