Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

Org Lett. 2015 Nov 6;17(21):5484-7. doi: 10.1021/acs.orglett.5b02851. Epub 2015 Oct 23.

Abstract

Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acylation
  • Catalysis
  • Hydrocarbons, Chlorinated / chemical synthesis*
  • Hydrocarbons, Chlorinated / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Propanols / chemistry*
  • Stereoisomerism

Substances

  • Hydrocarbons, Chlorinated
  • Indoles
  • Propanols
  • hexafluoroisopropanol