6533b824fe1ef96bd1280c55
RESEARCH PRODUCT
Favoring alkane primary carbon-hydrogen bond functionalization in supercritical carbon dioxide as reaction medium
Ana CaballeroJeymy T. SarmientoGregorio AsensioTomás R. BelderrainPedro J. PérezTeresa VareaAndrea Olmossubject
Alkanechemistry.chemical_classificationSupercritical carbon dioxideRenewable Energy Sustainability and the EnvironmentGeneral Chemical EngineeringAlkaneCarbon–hydrogen bond activation02 engineering and technologyGeneral Chemistry010402 general chemistry021001 nanoscience & nanotechnology01 natural sciences0104 chemical sciencesCatalysisHexanechemistry.chemical_compoundchemistryEthyl diazoacetateCarbon dioxidePolymer chemistryEnvironmental Chemistry0210 nano-technologyCarbon-hydrogenCarbeneEthyl heptanoatedescription
The selectivity of a catalytic alkane functionalization process can be modified just changing the reaction medium from neat alkane to supercritical carbon dioxide (scCO2). A silica supported copper complex bearing an Nheterocyclic carbene ligand promotes the functionalization of carbon-hydrogen bonds of alkanes by transferring the CHCO2Et group from N2=CHCO2Et (ethyl diazoacetate, EDA). In neat hexane only 3% of the primary C-H bonds (ethyl heptanoate being the product) are functionalized in that manner, whereas the same reaction carried out in scCO2 provides a 30% yield in this linear ester. Such effect seems to be induced by an electronic density flux from the NHC ligand to the surrounding carbon dioxide molecules.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-02-20 |