Direct Synthesis of Carbamoyl Fluorides by CO2 Deoxyfluorination

Herein, a new concept for the direct synthesis of carbamoyl fluoride derivatives is disclosed. The developed method makes use of CO2 as an inexpensive and abundant C1 source; a variety of amines were successfully converted in the presence of a deoxyfluorinating reagent. The corresponding products we...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-09, Vol.58 (36), p.12545-12548
Main Authors: Onida, Killian, Tlili, Anis
Format: Article
Language:English
Subjects:
Amines
carbamoyl fluorides
Carbon dioxide
deoxyfluorination
Fluorides
fluorine
Reagents
Synthesis
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Summary:Herein, a new concept for the direct synthesis of carbamoyl fluoride derivatives is disclosed. The developed method makes use of CO2 as an inexpensive and abundant C1 source; a variety of amines were successfully converted in the presence of a deoxyfluorinating reagent. The corresponding products were often obtained in excellent yields under mild reaction conditions (1 atm and room temperature). The reaction was easily scaled up, demonstrating the efficiency of the developed process. CO2 deoxyfluorination: The reductive fluorination of CO2 enables the synthesis of carbamoyl fluorides. The reactions are easily scalable, and the concept was exploited for the synthesis of 13C‐labeled carbamoyl compounds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201907354