4.7 Article

Nucleophilic Trifluoromethylation of Carbonyl Compounds: Trifluoroacetaldehyde Hydrate as a Trifluoromethyl Source

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 7, Pages 3300-3305

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo400202w

Keywords

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Funding

  1. Loker Hydrocarbon Research Institute
  2. NSF [DBI-0821671, CHE-0840366]
  3. NIH [S10 RR25432]
  4. University of Southern California Center for High-Performance Computing and Communications

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A feasible nucleophilic trifluoromethylating protocol has been developed using trifluoroacetaldehyde hydrate as an atom-economical trifluoromethyl source. The reaction was found to be applicable to the nucleophilic trifluoromethylation of a broad spectrum of carbonyl compounds with satisfactory yields in general. DFT calculations have been performed to provide mechanistic insight into methoxyethanol and hexafluoroacetone hydrate.

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