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Regioselective Synthesis of Isocoumarins via Iridium(III)-Catalyzed Oxidative Cyclization of Aromatic Acids with Propargyl Alcohols
Published in American Chemical Society
2019
PMID: 30730138
Volume: 84
   
Issue: 5
Pages: 2699 - 2712
Abstract
An Ir(III)-catalyzed oxidative cyclization of benzoic acids with propargyl alcohols to give substituted isocoumarins in a highly regioselective manner is described. This protocol has a broad substrate scope with high functional group tolerance. The observed isocoumarins were converted into biologically active tetracyclic indeno[2,1-c]isocoumarins by Lewis acid-mediated cyclization. A possible reaction mechanism is proposed and strongly supported by the detailed mechanistic investigation and DFT. © 2019 American Chemical Society.
About the journal
JournalData powered by TypesetJournal of Organic Chemistry
PublisherData powered by TypesetAmerican Chemical Society
ISSN00223263
Open AccessNo
Concepts (23)
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    Benzoic acid
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    Catalysis
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    Iridium compounds
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    Regioselectivity
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    ISOCOUMARINS
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    Lewis acid
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    OXIDATIVE CYCLIZATION
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    Propargyl alcohol
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    Reaction mechanism
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    Regio-selective
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    Regioselective synthesis
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    Cyclization
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    Alcohol derivative
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    Aromatic carboxylic acid
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    Benzoic acid derivative
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    Iridium
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    ISOCOUMARIN DERIVATIVE
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    PROPARGYL ALCOHOL DERIVATIVE
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    TETRACYCLIC INDENO[2,1 C]ISOCOUMARIN DERIVATIVE
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    Unclassified drug
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    Aerobic metabolism
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    Article
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    Chemical structure