ArticleOrganic letters2016
The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics.
Article in Organic letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 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
19 citing papers in PubMed.
- A Click-Type Reaction of (RRR)-α-Tocopherol and Related 6-Chromanols Allowing a One Pot Derivatisation of All Fat-Soluble Vitamins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- New Antibacterial and Antioxidant Chitin Derivatives: Ultrasonic Preparation and Biological Effects.Polymers · 2024Article
- Cycloadditions of Benzynes with the Azoxy [RN═NOrganic letters · 2024Article
- Cascade Aryne Aminoarylation for Biaryl Phenol Synthesis.Organic letters · 2024Article
- Ferrocenyl conjugated oxazepines/quinolines: multiyne coupling and ring-expanding or rearrangement.Frontiers in chemistry · 2024Article
- 1,3-Butadiynamides the Ethynylogous Ynamides: Synthesis, Properties and Applications in Heterocyclic Chemistry.Molecules (Basel, Switzerland) · 2023Review
- Silicon as a powerful control element in HDDA chemistry: redirection of innate cyclization preferences, functionalizable tethers, and formal bimolecular HDDA reactions.Chemical science · 2021Article
- Mechanistic and Kinetic Factors of ortho-Benzyne Formation in Hexadehydro-Diels-Alder (HDDA) Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- "Kobayashi Benzynes" as Hexadehydro-Diels-Alder Diynophiles.Organic letters · 2021Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- The Aza-hexadehydro-Diels-Alder Reaction.Journal of the American Chemical Society · 2019Article
- Reactions of thermally generated benzynes with six-memberedChemical science · 2019Article
- Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity.Chemical science · 2019Article
- Divergent Reactivity during the Trapping of Benzynes by Glycidol Analogs: Ring Cleavage via Pinacol-Like Rearrangements vs Oxirane Fragmentations.Organic letters · 2019Article
- Alder-ene reactions driven by high steric strain and bond angle distortion to form benzocyclobutenes.Chemical science · 2019Article
- Reactions of Diaziridines with Benzynes Give N-Arylhydrazones.Organic letters · 2018Article
- CuAngewandte Chemie (International ed. in English) · 2018Article
- Mechanistic Duality in Tertiary Amine Additions to Thermally Generated Hexadehydro-Diels-Alder Benzynes.Organic letters · 2017Article
- Reactions of hexadehydro-Diels-Alder benzynes with structurally complex multifunctional natural products.Nature chemistry · 2017Article
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
Abstract
Benzynes produced thermally by the cycloisomerization of triyne-containing precursors [i.e., by the hexadehydro-Diels-Alder (HDDA) reaction] react with phenols at the carbon ortho to the hydroxyl in an enelike fashion. Following tautomerization of the intermediate cyclohexadienones, this produces biaryl derivatives. DFT calculations of model reactions support this mechanistic interpretation. Substituted, unsymmetrical phenols and bis-phenols react in a fashion that can be explained by engagement of the most readily available (non-hydrogen-bonded) hydroxyl in the phenol-ene process.
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.