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Facile Access to AgOCF<sub>3</sub> and Its New Applications as a Reservoir for OCF<sub>2</sub> for the Direct Synthesis of N−CF<sub>3</sub>, Aryl or Alkyl Carbamoyl Fluorides

Abdurrahman Türksoy, Thomas Scattolin, Samir Bouayad‐Gervais, Franziska Schoenebeck

2020Chemistry - A European Journal60 citationsDOI

Abstract

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 AgOCF 3 at room temperature and showcase its performance in trifluoromethoxylations or as reservoir for O=CF 2 . This enabled the direct, practical and safe synthesis of valuable N‐alkyl/aryl and N−CF 3 carbamoyl fluorides from secondary amines and isothiocyanides, respectively. Our mechanistic data indicate that AgOCF 3 does not liberate O=CF 2 until it is activated by a nucleophilic co‐reagent, reinforcing the stability of the salt under our new preparation strategy.

Topics & Concepts

ReagentArylAlkylNucleophileSalt (chemistry)Combinatorial chemistryChemistryOrganic chemistryCatalysisFluorine in Organic ChemistryInorganic Fluorides and Related Compounds
Facile Access to AgOCF<sub>3</sub> and Its New Applications as a Reservoir for OCF<sub>2</sub> for the Direct Synthesis of N−CF<sub>3</sub>, Aryl or Alkyl Carbamoyl Fluorides | Litcius