Abstract
A tandem Cu-catalyzed oxidation-intramolecular Cannizzaro reaction leading to bioactive α-hydroxyesters from α-hydroxyketones is reported. The process uses oxygen as a sole oxidant to achieve the formation of glyoxals, which are efficiently converted in situ to important α-hydroxyesters. The mechanistic insights are provided by isotopic labeling and supported by DFT calculations. The transformation proved a robust synthetic tool to achieve the synthesis of human metabolites and hydroxyl esters of various biologically active steroid derivatives.
| Original language | English |
|---|---|
| Article number | e202400013 |
| Journal | ChemSusChem |
| Volume | 17 |
| Issue number | 13 |
| Early online date | 2024 |
| DOIs | |
| Publication status | Published - Jul 2024 |
| Publication type | A1 Journal article-refereed |
Funding
. The authors acknowledge the National Scientific Program “VIHREN” (grant KП‐06‐ДB‐1). The project leading to this application has received funding from the European Union's Horizon 2020 research and innovation programme under grant agreement No 951996. This work received financial support from PT national funds (FCT/MCTES, Fundação para a Ciência e Tecnologia and Ministério da Ciência, Tecnologia e Ensino Superior) through the project UIDB/50006/2020 | UIDP/50006/2020 and PTDC/QUI‐QOR/1131/2020. N. R. C. acknowledges FCT for the CEEC‐INST/2018.. CSC‐IT Center for Science Ltd, Finland is acknowledged for the allocation of computational resources. The authors are grateful to INFRAMAT project (part of the Bulgarian National Roadmap for research infrastructure, supported by the Bulgarian Ministry of Education and Science) for some of the research equipment that was used in this investigation. Dr. Rafael Gomes is acknowledged for the HRMS analysis
| Funders | Funder number |
|---|---|
| Fundação para a Ciência e a Tecnologia | |
| Ministry of Science and Higher Education | |
| Ministério da Ciência, Tecnologia e Ensino Superior | CEEC‐INST/2018, UIDP/50006/2020, PTDC/QUI‐QOR/1131/2020, UIDB/50006/2020 |
| Horizon 2020 | 951996 |
Keywords
- Biorefinery
- Cannizzaro reaction
- Copper catalysis
- Homogeneous catalysis
- Oxidation
Publication forum classification
- Publication forum level 2
ASJC Scopus subject areas
- Environmental Chemistry
- General Chemical Engineering
- General Materials Science
- General Energy