Premium
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
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom