ArticleAngewandte Chemie (International ed. in English)2022
Arene Activation through Iminium Ions: Product Diversity from Intramolecular Photocycloaddition Reactions.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 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.
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.
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Who cites it
5 citing papers in PubMed.
- Substrate-Controlled Dearomative Cycloadditions of Perfluoronaphthalenes via Visible-Light Energy Transfer Catalysis: Switchable Access to [2+2], [4+2], and Diastereoconvergent Cycloadducts.Angewandte Chemie (International ed. in English) · 2026Article
- Photochemical reactions of biomass derived platform chemicals.Frontiers in chemistry · 2024Review
- Rejuvenation of dearomative cycloaddition reactionsChemical science · 2023Review
- Chiral Lewis acid catalysis in a visible light-triggered cycloaddition/rearrangement cascade.Chemical science · 2022Article
- Arene Activation through Iminium Ions: Product Diversity from Intramolecular Photocycloaddition Reactions.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
While 2-alk-ω-enyloxy-sustituted benzaldehydes do not display any photochemical reactivity at the arene core, the respective iminium perchlorates were found to undergo efficient reactions either upon direct irradiation (λ=366 nm) or under sensitizing conditions (λ=420 nm, 2.5 mol% thioxanthen-9-one). Three pathways were found: (a) Most commonly, the reaction led to benzoxacyclic products in which the olefin in the tether underwent a formal, yet unprecedented carboformylation (13 examples, 44-99 % yield). The cascade process occurred with high diastereoselectivity and was found to be stereoconvergent. (b) If a substituent resides in the 3-position of the benzene ring, a meta photocycloaddition was observed which produced tetracyclic skeletons with five stereogenic centers in excellent regio- and diastereoselectivity (2 examples, 58-79 % yield). (c) If the tether was internally substituted at the alkene, an arene photocycloaddition was avoided and an azetidine was formed in an aza Paternò-Büchi reaction (2 examples, 95-98 % yield).
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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.