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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 N-heterocyclic 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 an effect seems to be induced by an electronic density flux from the NHC ligand to the surrounding carbon dioxide molecules.

Favoring Alkane Primary Carbon–Hydrogen Bond Functionalization in Supercritical Carbon Dioxide as Reaction Medium