Facile Access to AgOCF3 and Its New Applications as a Reservoir for OCF2 for the Direct Synthesis of N-CF3 , Aryl or Alkyl Carbamoyl Fluorides.

ABSTRACT

The development of innovative fluorination strategies is greatly dependent also on the availability, safety and practicability of available fluorinating reagents. We herein show a straightforward and quantitative strategy for the preparation of valuable AgOCF3 at room temperature and showcase its performance in trifluoromethoxylations or as reservoir for O=CF2 . This enabled the direct, practical and safe synthesis of valuable N-alkyl/aryl and N-CF3 carbamoyl fluorides from secondary amines and isothiocyanides, respectively. Our mechanistic data indicate that AgOCF3 does not liberate O=CF2 until it is activated by a nucleophilic co-reagent, reinforcing the stability of the salt under our new preparation strategy.