2021年7月
Synthesis of Difluoroglycine Derivatives from Amines, Difluorocarbene, and CO2: Computational Design, Scope, and Applications
CHEMISTRY-A EUROPEAN JOURNAL
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- 巻
- 27
- 号
- 39
- 開始ページ
- 10040
- 終了ページ
- 10047
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/chem.202100812
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
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 CO2. 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 degrees 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.
- リンク情報
- ID情報
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- DOI : 10.1002/chem.202100812
- ISSN : 0947-6539
- eISSN : 1521-3765
- ORCIDのPut Code : 103290245
- Web of Science ID : WOS:000655523700001