ArticleJournal of the American Chemical Society2022
Hydrogen Bonding Phase-Transfer Catalysis with Alkali Metal Fluorides and Beyond.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
17 citing papers in PubMed.
- PyOrbb-Automated Analyses of Orbital-Interaction Mechanisms.Journal of computational chemistry · 2026Article
- Synergistic Transition Metal and Hydrogen Bonding Phase-Transfer Catalysis Enables Enantioconvergent Allylic Fluorination with KF.Journal of the American Chemical Society · 2026Article
- Peptidic Catalysts Conformationally Tuned for Fluoride Binding and Delivery.Journal of the American Chemical Society · 2026Article
- Fluoride-Transfer Asymmetric Allylic Alkylation Enables Regiodivergent, Stereoselective Cross-Electrophile Coupling.Angewandte Chemie (International ed. in English) · 2026Article
- Hydrogen Bond Benchmark: Focal-Point Analysis and Assessment of DFT Functionals.Journal of computational chemistry · 2025Article
- Nucleophilic Fluorination of a Secondary Alkyl Bromide with KF(18-Crown-6) and Bulky Diols: Microsolvation Causes Chemoselectivity Inversion in the Free Energy Profile.ChemPlusChem · 2025Article
- Effects of Hydrogen Bonding Solvation by Diverse Fluorinated Bulky Alcohols on the Reaction Rate and Selectivity in Crown Ether Mediated Nucleophilic Fluorination in an Aprotic Solvent.ACS organic & inorganic Au · 2025Article
- Contact ion-pair SNature communications · 2025Article
- AMPA and NMDA Receptors in Hippocampus of Rats with Fluoride-Induced Cognitive Decline.International journal of molecular sciences · 2024Article
- Asymmetric phase-transfer catalysis.Nature reviews. Chemistry · 2024Review
- "Hydridic Hydrogen-Bond Donors" Are Not Hydrogen-Bond Donors.Journal of the American Chemical Society · 2024Article
- A review of frustrated Lewis pair enabled monoselective C-F bond activation.Chemical science · 2024Review
- Co-Catalyzed Hydrofluorination of Alkenes: Photocatalytic Method Development and Electroanalytical Mechanistic Investigation.Journal of the American Chemical Society · 2024Article
- Optimal Reference Genes for RT-qPCR Experiments in Hippocampus and Cortex of Rats Chronically Exposed to Excessive Fluoride.Biological trace element research · 2024Article
- Stereoselective Synthesis of Fluoroalkanes via FLP Mediated Monoselective C─F Activation of Geminal Difluoroalkanes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- A chiral pentanidium and pyridinyl-sulphonamide ion pair as an enantioselective organocatalyst for Steglich rearrangement.Chemical science · 2023Article
- Molecular Understanding and Practical In Silico Catalyst Design in Computational Organocatalysis and Phase Transfer Catalysis-Challenges and Opportunities.Molecules (Basel, Switzerland) · 2023Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
2 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Phase-transfer catalysis (PTC) is one of the most powerful catalytic manifolds for asymmetric synthesis. Chiral cationic or anionic PTC strategies have enabled a variety of transformations, yet studies on the use of insoluble inorganic salts as nucleophiles for the synthesis of enantioenriched molecules have remained elusive. A long-standing challenge is the development of methods for asymmetric carbon-fluorine bond formation from readily available and cost-effective alkali metal fluorides. In this Perspective, we describe how H-bond donors can provide a solution through fluoride binding. We use examples, primarily from our own research, to discuss how hydrogen bonding interactions impact fluoride reactivity and the role of H-bond donors as phase-transfer catalysts to bring solid-phase alkali metal fluorides in solution. These studies led to hydrogen bonding phase-transfer catalysis (HB-PTC), a new concept in PTC, originally crafted for alkali metal fluorides but offering opportunities beyond enantioselective fluorination. Looking ahead, the unlimited options that one can consider to diversify the H-bond donor, the inorganic salt, and the electrophile, herald a new era in phase-transfer catalysis. Whether abundant inorganic salts of lattice energy significantly higher than those studied to date could be considered as nucleophiles, e.g., CaF
Indexed as
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.