Insertion of CO2 into C–H Bonds

Insertion of CO2 into C–H Bonds

Author: Chemistry – A European Journal

Sustainable and efficient methods for the use of CO2 in the chemical industry have been highly sought after. However, current strategies for C–C bond-forming reactions with CO2 as a C1 building block are based on prefunctionalized compounds, which inevitably leads to salt waste and limits the sustainability of such methods.

Lukas J. Gooßen, Ruhr-Universität Bochum, Germany, and colleagues have developed a salt-free strategy for CO2 insertion into non-activated C–H bonds. They found that a copper(I) catalyst can enable the reaction of terminal alkynes with CO2 in the presence of a mild base, in this case, an amine. The resulting ammonium salt is less stable than inorganic carboxylates. Therefore, it can be hydrogenated to the primary alcohol with a rhodium/molybdenum catalyst. In this step, only water is released and the regenerated amine can be recovered, making the overall process waste-free.

This work demonstrates the feasibility of salt-free CO2 conversion by means of C–C bond formation. It provides a general strategy for the transformation of any reaction leading to an ammonium carboxylate into a salt-free hydroxymethylation process.


 

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