Fluorinated Vilsmeier Reagent: TFEDMA-mediated Synthesis of Aryl-cyanides and Aryl-amides via the Activation of Oximes dagger

A convenient method for the activation of aryl-oximes is reported using 1,1,2,2-tetrafluoro-N,N-dimethylethylamine (TFEDMA) as a scalable and efficient reagent. Aryl-aldoximes led to aryl-cyanides while aryl-ketoximes provided aryl-amides in moderate to excellent yields. The iminium form of TFEDMA acted as a fluorinated version of the well-known Vilsmeier reagent. Aryl cyanides and aryl amides are valuable synthetic units in natural products and drug candidates. The cyano group is also useful in polymer chemistry for the preparation of photovoltaic cells and LEDs.

Automated summary

A convenient method for the activation of aryl-oximes using TFEDMA as a scalable and efficient reagent is reported. Aryl-aldoximes led to aryl-cyanides, while aryl-ketoximes provided aryl-amides in moderate to excellent yields. The iminium form of TFEDMA acted as a fluorinated version of the well-known Vilsmeier reagent. Aryl cyanides and aryl amides are valuable synthetic units in natural products and drug candidates.