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An Expedient Method for the Umpolung Coupling of Enols with Heteronucleophiles
- Publication Year :
- 2022
-
Abstract
- [EN] In this paper, we present an unprecedented and general umpolung protocol that allows the functionalization of silyl enol ethers and of 1,3-dicarbonyl compounds with a large range of heteroatom nucleophiles, including carboxylic acids, alcohols, primary and secondary amines, azide, thiols, and also anionic carbamates derived from CO2. The scope of the reaction also extends to carbon-based nucleophiles. The reaction relies on the use of 1-bromo-3,3-dimethyl-1,3-dihydro-1 lambda(3)[d][1,2]iodaoxole, which provides a key alpha-brominated carbonyl intermediate. The reaction mechanism has been studied experimentally and by DFT, and we propose formation of an unusual enolonium intermediate with a halogen-bonded bromide.
Details
- Database :
- OAIster
- Notes :
- The authors are grateful for support from the Swedish Research Council through Vetenskapsradet, and from the Goran Gustafsson Foundation. This project was also funded by the European Union's Horizon 2020 research and innovation programme under Grant Agreement 721223 and NordForsk through NordCO2 (85378)., English
- Publication Type :
- Electronic Resource
- Accession number :
- edsoai.on1346951654
- Document Type :
- Electronic Resource