4.8 Article

Iron-Catalyzed Tandem Three-Component Alkylation: Access to α-Methylated Substituted Ketones

Journal

ORGANIC LETTERS
Volume 21, Issue 9, Pages 3057-3061

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00630

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Funding

  1. Ministere de la Recherche et des Nouvelles Technologies, Normandie Universite, CNRS, Region Normandie
  2. LABEX SynOrg [ANR-11-LABX-0029]
  3. Cooperation Francaise-Senegal

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The borrowing hydrogen strategy has been applied in the synthesis of alpha-branched methylated ketones via a tandem three-component reaction catalyzed by a diaminocyclopentadienone iron tricarbonyl complex. Various alkyl and aromatic methyl ketones underwent dialkylation with various primary alcohols and methanol as alkylating agents in mild reaction conditions and good yields. Deuterium labeling experiments suggested that the benzylic alcohol was the hydrogen source in this tandem process.

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