4.8 Article

Selective O-Difluoromethylation of 1,3-Diones by Bromodifluoromethylating Reagents

Journal

ORGANIC LETTERS
Volume 15, Issue 5, Pages 1044-1047

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol4000313

Keywords

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Funding

  1. Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology, Japan
  2. MEXT (Ministry of Education, Culture, Sports, Science and Technology) [24105513, 2304]
  3. JST (ACT-C: Creation of Advanced Catalytic Transformation for the Sustainable Manufacturing at Low Energy, Low Environmental Load)
  4. Tosoh F-Tech Ltd.
  5. Hori Sciences & Arts Foundation
  6. Grants-in-Aid for Scientific Research [24105513] Funding Source: KAKEN

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The regioselective Odifluoromethylation of 1,3-diones was achieved via in situ generation of difluorocarbene from bromodifluoromethylating reagents in the presence of an organic base. A wide variety of difluormethyl enol ethers were obtained in good to excellent yields. The reaction mechanism is discussed based on ab initio calculations (kcal/mol).

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