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Light‐Driven Carbene Catalysis for the Synthesis of Aliphatic and α‐Amino Ketones.
- Source :
- Angewandte Chemie International Edition; 8/9/2021, Vol. 60 Issue 33, p17925-17931, 7p
- Publication Year :
- 2021
-
Abstract
- Single‐electron N‐heterocyclic carbene (NHC) catalysis has gained attention recently for the synthesis of C−C bonds. Guided by density functional theory and mechanistic analyses, we report the light‐driven synthesis of aliphatic and α‐amino ketones using single‐electron NHC operators. Computational and experimental results reveal that the reactivity of the key radical intermediate is substrate‐dependent and can be modulated through steric and electronic parameters of the NHC. Catalyst potential is harnessed in the visible‐light driven generation of an acyl azolium radical species that undergoes selective coupling with various radical partners to afford diverse ketone products. This methodology is showcased in the direct late‐stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single‐electron NHC operators. [ABSTRACT FROM AUTHOR]
- Subjects :
- KETONES
DENSITY functional theory
CARBENES
CARBENE synthesis
CATALYSIS
AMINO acids
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 60
- Issue :
- 33
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 151721372
- Full Text :
- https://doi.org/10.1002/anie.202105354