Catalyst-Free Transfer Hydrogenation of Activated Alkenes Exploiting Isopropanol as the Sole and Traceless Reductant.
| Autor: | Das TK; Department of Chemistry, Rice University, Houston, Texas 77030, USA., Rodriguez Treviño AM; Department of Chemistry, Rice University, Houston, Texas 77030, USA., Pandiri S; Department of Chemistry, Rice University, Houston, Texas 77030, USA., Irvankoski S; Department of Chemistry and Materials Science, Aalto University, FI-02150 Espoo, Finland., Siito-Nen JH; Department of Chemistry and Materials Science, Aalto University, FI-02150 Espoo, Finland., Rodriguez SM; Department of Natural Sciences, University of North Texas at Dallas, Dallas, Texas 75241, USA., Yousufuddin M; Department of Natural Sciences, University of North Texas at Dallas, Dallas, Texas 75241, USA., Kürti L; Department of Chemistry, Rice University, Houston, Texas 77030, USA. |
|---|---|
| Jazyk: | angličtina |
| Zdroj: | Green chemistry : an international journal and green chemistry resource : GC [Green Chem] 2023 Jan 21; Vol. 25 (2), pp. 746-754. Date of Electronic Publication: 2023 Jan 04. |
| DOI: | 10.1039/d2gc04315g |
| Abstrakt: | Both metal-catalyzed and organocatalytic transfer hydrogenation reactions are widely employed for the reduction of C=O and C=N bonds. However, selective transfer hydrogenation reactions of C=C bonds remain challenging. Therefore, the chemoselective transfer hydrogenation of olefins under mild conditions and in the absence of metal catalysts, using readily available and inexpensive reducing agents (i.e. primary and secondary alcohols), will mark a significant advancement towards the development of green transfer hydrogenation strategies. Described herein is an unconventional catalyst-free transfer hydrogenation reaction of activated alkenes using isopropanol as an eco-friendly reductant and solvent. The reaction gives convenient synthetic access to a wide range of substituted malonic acid half oxyesters (SMAHOs) in moderate to good yields. Mechanistic investigations point towards an unprecedented hydrogen bond-assisted transfer hydrogenation process. Competing Interests: Conflicts of interest The authors declare no conflicts of interest. |
| Databáze: | MEDLINE |
| Externí odkaz: |
|