ArticleAngewandte Chemie (International ed. in English)2019
Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- One-pot divergent synthesis of 5-arylmethyl oxazoles and polyacenes from propargylic amides and arynes.Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones.Organic letters · 2024Article
- Evaluation of Retro-Aldol vs Retro-Carbonyl-Ene Mechanistic Pathways in a Complexity-Generating C-C Bond Fragmentation.Organic letters · 2024Article
- Generation and reactivity of unsymmetrical strained heterocyclic allenes.Nature synthesis · 2024Article
- Facile synthesis of 2-aza-9,10-diphenylanthracene and the effect of precise nitrogen atom incorporation on OLED emitters performance.Materials advances · 2023Article
- Total Synthesis of Phenanthroindolizidines Using Strained Azacyclic Alkynes.Organic letters · 2023Article
- Catalyst-Controlled Annulations of Strained Cyclic Allenes with π-Allylpalladium Complexes.Journal of the American Chemical Society · 2023Article
- π-Extension of heterocyclesChemical science · 2022Article
- Cycloaddition Cascades of Strained Alkynes and Oxadiazinones.Angewandte Chemie (International ed. in English) · 2021Article
- Review
- Coumarin (5,6-Benzo-2-pyrone) Trapping of an HDDA-Benzyne.Organic letters · 2021Article
- Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene.Organic letters · 2020Article
- Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.Angewandte Chemie (International ed. in English) · 2020Review
- Safety Assessment of Benzyne Generation from a Silyl Triflate Precursor.Organic letters · 2020Article
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3 authors.
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Abstract
We report a modular synthetic strategy for accessing heteroatom-containing polycyclic aromatic hydrocarbons (PAHs). Our approach relies on the controlled generation of transient heterocyclic alkynes and arynes. The strained intermediates undergo in situ trapping with readily accessible oxadiazinones. Four sequential pericyclic reactions occur, namely two Diels-Alder/retro-Diels-Alder sequences, which can be performed in a stepwise or one-pot fashion to assemble four new carbon-carbon (C-C) bonds. These studies underscore how the use of heterocyclic strained intermediates can be harnessed for the preparation of new organic materials.
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