ArticleJournal of the American Chemical Society2016
Quantification of the Electrophilicity of Benzyne and Related Intermediates.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Molecular Rotors as Reactivity Probes: Predicting Electrophilicity from the Speed of Rotation.Angewandte Chemie (International ed. in English) · 2025Article
- A strategy to access unprecedented reactive intermediates featuring carbenes, carbocations, biradicals, and inverted σ-bonds via hypervalent λProceedings of the Japan Academy. Series B, Physical and biological sciences · 2025Review
- Bromothiolation of Arynes for the Synthesis of 2-Bromobenzenethiol Equivalents.Organic letters · 2024Article
- Switchable chemoselective aryne reactions between nucleophiles and pericyclic reaction partners using either 3-methoxybenzyne or 3-silylbenzyne.Nature communications · 2024Article
- Nickel binding enables isolation and reactivity of previously inaccessible 7-aza-2,3-indolynes.Science (New York, N.Y.) · 2024Article
- Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides.Organic letters · 2024Article
- An efficient and chemoselective method to generate arynes.Chemical science · 2023Article
- Empowering boronic acids as hydroxyl synthons for aryne induced three-component coupling reactions.Chemical science · 2023Article
- The Aryne Phosphate Reaction.Angewandte Chemie (International ed. in English) · 2022Article
- Review
- Article
- Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds.Angewandte Chemie (International ed. in English) · 2019Article
- Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.The Journal of organic chemistry · 2019Article
- Arynes and Cyclic Alkynes as Synthetic Building Blocks for Stereodefined Quaternary Centers.Journal of the American Chemical Society · 2018Article
- Blue-Emitting Arylalkynyl Naphthalene Derivatives via a Hexadehydro-Diels-Alder Cascade Reaction.Journal of the American Chemical Society · 2016Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
The determination of reactivity parameters for short-lived intermediates provides an indispensable tool for synthetic design. Despite that electrophilicity parameters have now been established for more than 250 reactive species, the corresponding parameters for benzyne and related intermediates have not been uncovered. We report a study that has allowed for the quantification of benzyne's electrophilicity parameter. Our approach relies on the strategic use of the diffusion-clock method and also provides electrophilicity parameters E for other substituted arynes.
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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.