In:
Chemistry – A European Journal, Wiley, Vol. 27, No. 39 ( 2021-07-12), p. 10040-10047
Kurzfassung:
A three‐component reaction (3CR) for the synthesis of difluoroglycine derivatives has been achieved by using amines, difluorocarbene (generated in situ), and the abundant, inexpensive, and nontoxic C 1 source CO 2 . Various tert ‐amines and pyridine, (iso)quinoline, imidazole, thiazole, and pyrazole derivatives were incorporated, and the corresponding products were isolated in solid form without purification by column chromatography on silica gel. Detailed reaction profiles of the 3CR were obtained from computational analysis using DFT calculations, and the results critically suggest that simple ammonia is not applicable to this reaction. In addition, as strongly supported by computational predictions, a new reagent that can generate difluorocarbene at 0 °C without any additives was discovered. Finally, radical substitution reactions of the obtained difluoroglycine derivatives under photoredox conditions, as well as a synthetic application as an N ‐heterocyclic carbene ligand are shown.
Materialart:
Online-Ressource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.202100812
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2021
ZDB Id:
1478547-X
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