ArticleCommunications chemistry2023
Chemoselective cycloisomerization of O-alkenylbenzamides via concomitant 1,2-aryl migration/elimination mediated by hypervalent iodine reagents.
Article in Communications chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Hypervalent iodine reagents in organic synthesis: a review of methodology developments and synthetic applications.RSC advances · 2026Review
- Electrooxidative Divergent Halocyclizations of Ambident Amides.Angewandte Chemie (International ed. in English) · 2026Article
- Ligand-Controlled Chemodivergent Bismuth Catalysis.Journal of the American Chemical Society · 2025Article
- Hypervalent Iodine-Catalyzed Fluorination of Diene-Containing Compounds: A Computational Study.Molecules (Basel, Switzerland) · 2024Article
- Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA.Beilstein journal of organic chemistry · 2024Article
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Authors and funding
4 authors.
Funding
Abstract
As an ambident nucleophile, controlling the reaction selectivities of nitrogen and oxygen atoms in amide moiety is a challenging issue in organic synthesis. Herein, we present a chemodivergent cycloisomerization approach to construct isoquinolinone and iminoisocoumarin skeletons from o-alkenylbenzamide derivatives. The chemo-controllable strategy employed an exclusive 1,2-aryl migration/elimination cascade, enabled by different hypervalent iodine species generated in situ from the reaction of iodosobenzene (PhIO) with MeOH or 2,4,6-tris-isopropylbenzene sulfonic acid. DFT studies revealed that the nitrogen and oxygen atoms of the intermediates in the two reaction systems have different nucleophilicities and thus produce the selectivity of N or O-attack modes.
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Registered trials
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