ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016
Structurally Divergent Lithium Catalyzed Friedel-Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2016. 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.
- Iron-Catalyzed Friedel-Crafts Reactions of Unactivated 3-Aryl-Oxetanols Exploiting HFIP Stabilization of Carbocations.The Journal of organic chemistry · 2026Article
- Synthesis ofThe Journal of organic chemistry · 2025Article
- Oxetanes: formation, reactivity and total syntheses of natural products.Beilstein journal of organic chemistry · 2025Review
- Harnessing Oxetane and Azetidine Sulfonyl Fluorides for Opportunities in Drug Discovery.Journal of the American Chemical Society · 2024Article
- Synthesis of 3,3-Disubstituted Thietane Dioxides.The Journal of organic chemistry · 2024Article
- Oxetanes in Drug Discovery Campaigns.Journal of medicinal chemistry · 2023Review
- Structure Guided Design, Synthesis, and Biological Evaluation of Oxetane-Containing Indole Analogues.Bioorganic & medicinal chemistry · 2023Article
- Visible Light Photoredox-Catalyzed Decarboxylative Alkylation of 3-Aryl-Oxetanes and Azetidines via Benzylic Tertiary Radicals and Implications of Benzylic Radical Stability.The Journal of organic chemistry · 2023Article
- Triflamides and Triflimides: Synthesis and Applications.Molecules (Basel, Switzerland) · 2022Review
- Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes.Organic letters · 2022Article
- Investigating 3,3-diaryloxetanes as potential bioisosteres through matched molecular pair analysis.RSC medicinal chemistry · 2021Article
- Recent Advances in Enantioselective Desymmetrizations of Prochiral Oxetanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Chemical Space Exploration of Oxetanes.International journal of molecular sciences · 2020Article
- 3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular annulation reactions.Chemical science · 2020Article
- Lithium-Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group.ACS medicinal chemistry letters · 2017Article
- Structurally Divergent Lithium Catalyzed Friedel-Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The first examples of 3,3-diaryloxetanes are prepared in a lithium-catalyzed and substrate dependent divergent Friedel-Crafts reaction. para-Selective Friedel-Crafts reactions of phenols using oxetan-3-ols afford 3,3-diaryloxetanes by displacement of the hydroxy group. These constitute new isosteres for benzophenones and diarylmethanes. Conversely, ortho-selective Friedel-Crafts reactions of phenols afford 3-aryl-3-hydroxymethyl-dihydrobenzofurans by tandem alkylation-ring-opening reactions; the outcome of the reaction diverging to structurally distinct products dependent on the substrate regioselectivity. Further reactivity of the oxetane products is demonstrated, suitable for incorporation into drug discovery efforts.
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.