ArticleJournal of the American Chemical Society2018
New Hindered Amide Base for Aryne Insertion into Si-P, Si-S, Si-N, and C-C Bonds.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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The trial behind it
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Who cites it
12 citing papers in PubMed, 65 citations in OpenAlex.
- Reppe-Type Regioselective Assembly of Meta-Teraryls using Phenyl Vinyl Sulfone as a Traceless Acetylene Surrogate.Organometallics · 2026Article
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- Aryne Generation from Aryl Halides Via Photothermal Red-Light Activation.Journal of the American Chemical Society · 2025Article
- An efficient and chemoselective method to generate arynes.Chemical science · 2023Article
- 3-sulfonyloxyaryl(mesityl)iodonium triflates as 1,2-benzdiyne precursors with activation via ortho-deprotonative elimination strategy.Nature communications · 2023Article
- Synthesis and Structural Properties of Adamantane-Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety.ChemistryOpen · 2022Article
- Article
- The Aryne Phosphate Reaction.Angewandte Chemie (International ed. in English) · 2022Article
- Arynes as Radical Acceptors: TEMPO-Mediated Cascades Comprising Addition, Cyclization, and Trapping.Angewandte Chemie (International ed. in English) · 2021Article
- One-step synthesis of benzo[Chemical science · 2020Article
- Isolation of an elusive phosphatetrahedrane.Science advances · 2020Article
- 1,2-Bis(arylthio)arene synthesis via aryne intermediates.Chemical communications (Cambridge, England) · 2019Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
A general method for a new, hindered lithium diadamantylamide (LDAM) base-promoted insertion of arynes into Si-P, Si-S, Si-N, and C-C bonds is described. Arynes are generated from easily available aryl triflates and halides. Subsequent reaction of the aryne with silylated phosphines, sulfides, or amines affords the insertion products. Furthermore, a one-step synthesis of anthracenes from aryl halides and aryl ketones is also demonstrated. Cyano, aryl, alkyl, trifluoromethyl, vinyl, methoxy, chloro, fluoro, and even formyl moieties are compatible with the reaction conditions. The new lithium amide affords higher yields compared with lithium tetramethylpiperidide (LiTMP)-promoted reactions. Furthermore, the bulkiness of LDAM base essentially suppresses aryne reaction with base, allowing use of aryl halides and triflates as the limiting reagents.
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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.