Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 10, Pages 2183-2186Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000116
Keywords
carbamoyl fluorides; fluorination; mechanism; N-trifluoromethyl; synthetic methods
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Funding
- RWTH Aachen University
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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.
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