ArticleOrganic & biomolecular chemistry2019
Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions.
Article in Organic & biomolecular chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 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
15 citing papers in PubMed, 49 citations in OpenAlex.
- Molecular engineering of bistetrafluoropyridine aryl ethers: a general platform for stable and programmable amorphous organic solids.RSC advances · 2026Article
- Enhanced crystallinity of tetrahalopyridyl (THP) derivatized compounds.Chemical science · 2026Article
- Tin can milling: low-tech mechanochemical synthesis of plant-based prepolymers incorporating perfluoropyridine.RSC advances · 2025Article
- Article
- Cooperative Anion-π and C-H-Cl Interactions in Multifunctional Naphthalene-Based Receptors for Chloride Recognition: Cage-Size Modulation Through Substitution Patterns.ChemPlusChem · 2024Article
- Halogenated Phenylpyridines Possessing Chemo-Selectivity for Diverse Molecular Architectures.ACS omega · 2024Article
- Synthesis and crystal structure of 2-[(2,3,5,6-tetra-fluoro-pyridin-4-yl)amino]-ethyl methacrylate.Acta crystallographica. Section E, Crystallographic communications · 2023Article
- Au(I) Catalyzed HF Transfer: Tandem Alkyne Hydrofluorination and Perfluoroarene Functionalization.ACS catalysis · 2022Article
- Perfluoropyridine: Discovery, Chemistry, and Applications in Polymers and Material Science.Molecules (Basel, Switzerland) · 2022Review
- Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Total Synthesis of the Natural Chalcone Lophirone E, Synthetic Studies toward Benzofuran and Indole-Based Analogues, and Investigation of Anti-Leishmanial Activity.Molecules (Basel, Switzerland) · 2022Article
- Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP).Organic letters · 2021Article
- Article
- Synthesis of complex unnatural fluorine-containing amino acids.Journal of fluorine chemistry · 2020Review
- Crystal structures and Hirshfeld surface analysis of a series of 4-Acta crystallographica. Section E, Crystallographic communications · 2019Article
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 at 1 institution in 2 countries.
Funding
Abstract
Phenols are extremely valuable building blocks in the areas of pharmaceuticals, natural products, materials and catalysts. In order to carry out modifications on phenols, the phenolic oxygen is routinely protected to prevent unwanted side reactions. Presently many of the protecting groups available can require harsh conditions, specialist equipment, expensive or air/moisture-sensitive reagents to install and remove. Here we introduce the use of the tetrafluoropyridyl (TFP) group as a general protecting group for phenols. TFP can be installed in one step with no sensitivity to water or air, and it is stable under a range of commonly employed reaction conditions including acid and base. The TFP protecting group is readily cleaved under mild conditions with quantitative conversion to the parent phenol, observed in many cases in less than 1 hour.
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.