Copper-mediated N-Trifluoromethylation of O-Benzoylhydroxylamines

Fleetwood, Thomas D. and Kerr, William J. and Mason, Joseph (2024) Copper-mediated N-Trifluoromethylation of O-Benzoylhydroxylamines. Chemistry - A European Journal, 30 (6). e202303314. ISSN 1521-3765 (https://doi.org/10.1002/chem.202303314)

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Abstract

The use of trifluoromethyl containing compounds is well established within medicinal chemistry, with a range of approved drugs containing C-CF3 and O-CF3 moieties. However, the utilisation of the N-CF3 functional group remains relatively unexplored. This may be attributed to the challenging synthesis of this unit, with many current methods employing harsh conditions or less accessible reagents. A robust methodology for the N-trifluoromethylation of secondary amines has been developed, which employs an umpolung strategy in the form of a copper-catalysed electrophilic amination. The method is operationally simple, uses mild, inexpensive reagents, and has been used to synthesise a range of novel, structurally complex N-CF3 containing compounds.

ORCID iDs

Kerr, William J. ORCID: https://orcid.org/0000-0002-1332-785X

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• Item metadata

  Item type:	Article
  ID code:	87548
  Dates:	Date Event 26 January 2024 Published 29 November 2023 Published Online 28 November 2023 Accepted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	08 Dec 2023 11:55
  Last modified:	12 Dec 2024 15:10
  URI:	https://strathprints.strath.ac.uk/id/eprint/87548