4.5 Article

A Simple Protocol from Benzalacetones to 1,1,1-Trifluoro-2,5-diketones and 2-(Trifluoromethyl)furans by Reductive Trifluoroacetylation

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 15, Pages 2237-2243

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000160

Keywords

Electron transfer; Magnesium; Trifluoroacetylation; Trifluoromethyl furans; Trifluoromethyl ketones

Funding

  1. JSPS KAKENHI Grant [22605003, 25410110, 16K05768]
  2. Grants-in-Aid for Scientific Research [22605003, 25410110, 16K05768] Funding Source: KAKEN

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A simple two-step access to 1,1,1-trifluoro-2,5-diketones and 2-(trifluoromethyl)furans was developed through magnesium-promoted reductive trifluoroacetylation of benzalacetones and acid-facilitated deacetalization. Two types of trifluoromethylated compounds were selectively synthesized from easily prepared aromatic conjugated enones and ethyl trifluoroacetate by control of reaction conditions in moderate to high yields with wide substrate tolerance.

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