A General Method for Imine Formation Using B(OCH2CF3)3

Org Lett. 2015 May 15;17(10):2442-5. doi: 10.1021/acs.orglett.5b00949. Epub 2015 Apr 23.

Abstract

Tris(2,2,2-trifluoroethyl)borate [B(OCH2CF3)3] was found to be a mild and general reagent for the formation of a variety of imines by condensation of amides or amines with carbonyl compounds. N-Sulfinyl, N-toluenesulfonyl, N-(dimethylamino)sulfamoyl, N-diphenylphosphinoyl, N-(α-methylbenzyl), and N-(4-methoxyphenyl) aldimines are all accessible using this reagent at room temperature. The reactions are operationally simple, and the products are obtained without special workup or isolation procedures.

MeSH terms

  • Borates / chemistry*
  • Hydrocarbons, Fluorinated / chemistry*
  • Imines / chemical synthesis*
  • Imines / chemistry
  • Molecular Structure

Substances

  • Borates
  • Hydrocarbons, Fluorinated
  • Imines
  • tris(2,2,2-trifluoroethyl)borate