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Deoxyfluorination of 1°, 2°, and 3° Alcohols by Nonbasic O-H Activation and Lewis Acid-Catalyzed Fluoride Shuttling.
Moon, Hye Won; Lavagnino, Marissa N; Lim, Soohyun; Palkowitz, Maximilian D; Mandler, Michael D; Beutner, Gregory L; Drance, Myles J; Lipshultz, Jeffrey M; Scola, Paul M; Radosevich, Alexander T.
Afiliación
  • Moon HW; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
  • Lavagnino MN; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
  • Lim S; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
  • Palkowitz MD; Small Molecule Drug Discovery, Bristol Myers Squibb, 250 Water Street, Cambridge, Massachusetts 02141, United States.
  • Mandler MD; Small Molecule Drug Discovery, Bristol Myers Squibb, Princeton, New Jersey 08543, United States.
  • Beutner GL; Chemical and Synthetic Development, Bristol Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Drance MJ; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
  • Lipshultz JM; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
  • Scola PM; Small Molecule Drug Discovery, Bristol Myers Squibb, 250 Water Street, Cambridge, Massachusetts 02141, United States.
  • Radosevich AT; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
J Am Chem Soc ; 145(41): 22735-22744, 2023 Oct 18.
Article en En | MEDLINE | ID: mdl-37812176
A method for deoxyfluorination of aliphatic primary, secondary, and tertiary alcohols is reported, employing a nontrigonal phosphorus triamide for base-free alcohol activation in conjunction with an organic soluble fluoride donor and a triarylborane fluoride shuttling catalyst. Mechanistic experiments are consistent with a reaction that proceeds by the collapse of an oxyphosphonium fluoroborate ion pair with fluoride transfer. The substrate scope complements existing deoxyfluorination methods and enables the preparation of homochiral secondary and tertiary alkylfluorides by stereoinversion of the substrate alcohol.

Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos

Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos