ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Electrochemical-Induced Ring Transformation of Cyclic α-(ortho-Iodophenyl)-β-oxoesters.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. 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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5 citing papers in PubMed.
- Mechanistic Insights into CYP199A4-Catalyzed α-Hydroxyketone Formation and Hydrogen Bond-Assisted C-C Bond Cleavage Catalyzed by the CYP199A4 F182L Mutant.International journal of molecular sciences · 2025Article
- Synthesis of Optically Active Spirocycles by a Sequence of Decarboxylative Asymmetric Allylic Alkylation and Heck Reaction.Organic letters · 2024Article
- Cathodic Corrosion of Metal Electrodes-How to Prevent It in Electroorganic Synthesis.Chemical reviews · 2021Article
- Visible-light-driven palladium-catalyzed Dowd-Beckwith ring expansion/C-C bond formation cascade.Chemical science · 2020Article
- Electrochemical-Induced Ring Transformation of Cyclic α-(ortho-Iodophenyl)-β-oxoesters.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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Abstract
Cyclic α-(ortho-iodophenyl)-β-oxoesters were converted in a ring-expanding transformation to furnish benzannulated cycloalkanone carboxylic esters. The reaction sequence started by electrochemical reduction of the iodoarene moiety. In a mechanistic rationale, the resulting carbanionic species was adding to the carbonyl group under formation of a strained, tricyclic benzocyclobutene intermediate, which underwent carbon-carbon bond cleavage and rearrangement of the carbon skeleton by retro-aldol reaction. The scope of the reaction sequence was investigated by converting cyclic oxoesters with different ring sizes yielding benzocycloheptanone, -nonanone and -decanone derivatives in moderate to good yields. Furthermore, acyclic starting materials and cyclic compounds carrying additional substituents on the iodophenyl ring were submitted to this reaction sequence. The starting materials for this transformation are straightforwardly obtained by conversion of β-oxoesters with phenyliodobis(trifluoroacetate).
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