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Facile Access to AgOCF 3 and Its New Applications as a Reservoir for OCF 2 for the Direct Synthesis of N−CF 3 , Aryl or Alkyl Carbamoyl Fluorides
Author(s) -
Turksoy Abdurrahman,
Scattolin Thomas,
BouayadGervais Samir,
Schoenebeck Franziska
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000116
Subject(s) - reagent , aryl , alkyl , nucleophile , salt (chemistry) , combinatorial chemistry , chemistry , organic chemistry , catalysis
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.