1. Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones.
- Author
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Bay AV, Fitzpatrick KP, González-Montiel GA, Farah AO, Cheong PH, and Scheidt KA
- Subjects
- Catalysis, Electrons, Ketones chemistry, Methane chemistry, Molecular Structure, Stereoisomerism, Heterocyclic Compounds chemistry, Ketones chemical synthesis, Light, Methane analogs & derivatives
- 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., (© 2021 Wiley-VCH GmbH.)
- Published
- 2021
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