Regioselective Transfer Hydrogenation of Substituted Oxiranes with Alcohols Using MgO as the Catalyst
Marek Gliński, Patrycja Waniek
TL;DR
This study demonstrates high regioselectivity in hydrogenating various oxiranes using magnesium oxide as a catalyst in the vapor phase.
Contribution
The study introduces MgO as an effective catalyst for vapor-phase CTH of substituted oxiranes with high regioselectivity.
Findings
Primary alcohols were the main products with high regioselectivity (93-100%) for methyl-, n-butyl-, and phenyloxirane.
Vapor-phase CTH of methyloxirane with 2-pentanol produced three products with yields of 48%, 4%, and 35%.
Phenyloxirane CTH yielded 95% 2-phenylethanol with minor byproducts.
Abstract
An excellent regioselectivity of vapor-phase catalytic transfer hydrogenation (CTH) of substituted oxiranes (methyl-, n-butyl-, and phenyloxirane) with alkanols (EtOH, 2-PrOH or 2-PeOH) as hydrogen donors in the presence of magnesium oxide as a catalyst was attained. In the vapor phase, all of these oxiranes as well as 1,2-epoxycyclohexane were hydrogenated. Moreover, it was found that primary alcohols were always the main products of CTH of methyl-, n-butyl-, and phenyloxirane with very good regioselectivity towards the alcohols: 93, 73, and 100%, respectively. It was shown that vapor-phase CTH of methyloxirane with 2-pentanol led to three products, two regioisomeric propanols, (1-PrOH and 2-PrOH), and also 1-(2-pentyloxy)-2-propanol. Their yields were 48%, 4%, and 35%, respectively. Two regioisomeric hexanols (1-HeOH, 54% yield and 2-HeOH, 20% yield) and 2-hexanone (14% yield) were…
Genes, proteins, chemicals, diseases, species, mutations and cell lines named across the full text — each resolved to its canonical identifier and authoritative record.
Click any figure to enlarge with its caption.
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9
Figure 10
Figure 11
Figure 12
Figure 13Peer Reviews
No public reviews on file for this paper yet. If you reviewed it on a platform where reviews are public (OpenReview, ICLR, NeurIPS, ICML), you can paste yours below so the community can read it here.
Videos
No videos yet. Explain this paper in a talk, walkthrough, or lecture? Add one.
Taxonomy
TopicsAsymmetric Hydrogenation and Catalysis · Catalysis for Biomass Conversion · Asymmetric Synthesis and Catalysis