ArticleJournal of the American Chemical Society2015
Phosphine-Mediated Iterative Arene Homologation Using Allenes.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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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.
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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.
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Who cites it
9 citing papers in PubMed.
- Generation of Mono- and BisazabicyclicOrganic letters · 2026Article
- Expanding Reaction Profile of Allyl Carboxylates via 1,2-Radical Migration (RaM): Visible-Light-Induced Phosphine-Catalyzed 1,3-Carbobromination of Allyl Carboxylates.Journal of the American Chemical Society · 2023Article
- Rational design of N-heterocyclic compound classes via regenerative cyclization of diamines.Nature communications · 2023Article
- Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CFBeilstein journal of organic chemistry · 2021Article
- Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.Angewandte Chemie (International ed. in English) · 2018Review
- Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.Chemical science · 2018Article
- Toward Generalization of Iterative Small Molecule Synthesis.Nature reviews. Chemistry · 2018Article
- From Mechanistic Study to Chiral Catalyst Optimization: Theoretical Insight into Binaphthophosphepine-catalyzed Asymmetric Intramolecular [3 + 2] Cycloaddition.Scientific reports · 2017Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted allenes in the presence of PPh2Et, naphthalene derivatives were also obtained in up to quantitative yields. The mechanism of the latter transformation is straightforward: aldol addition followed by Wittig olefination and dehydration. The mechanism of the former is a tandem γ-umpolung/aldol/Wittig/dehydration process, as established by preparation of putative reaction intermediates and mass spectrometric analysis. This transformation can be applied iteratively to prepare anthracenes and tetracenes using carboxylic acids as pronucleophiles.
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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.