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RESEARCH PRODUCT

Discovering Copper for Methane C–H Bond Functionalization

Tomás R. BelderrainAndrea OlmosEleuterio ÁLvarezPedro J. PérezAna CaballeroTeresa VareaBárbara NovergesGregorio AsensioRiccardo Gava

subject

Supercritical carbon dioxideTrifluoromethylchemistry.chemical_elementButaneGeneral ChemistryMedicinal chemistryCopperCatalysisMethaneCatalysischemistry.chemical_compoundchemistryEthyl diazoacetatePropaneOrganic chemistry

description

The copper complex Tp(CF3)2,BrCu(NCMe) (1, Tp(CF3)2,Br = hydrotris((3,5-bis(trifluoromethyl)-4-bromo)-pyrazol-1-yl)borate) catalyzes the insertion of the CHCO2Et group (from ethyl diazoacetate N2CHCO2Et, EDA) into the C–H bonds of methane, in a homogeneous process that uses supercritical carbon dioxide (scCO2) as the reaction medium. Other light alkanes such as ethane, propane, and butane have been also functionalized with this copper-based catalyst, in the first example of the derivatization of the series of C1–C4 alkanes with this metal and a soluble catalyst.

https://doi.org/10.1021/acscatal.5b00718