Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones
Year: 2025
Type: article
Abstract: Converting carbon dioxide (CO2) into valuable heterocycles is of great synthetic value but is usually limited to five- and six-membered ring compounds. Here, we report a catalytic approach for transforming this carbon renewable into seven-membered heterocycles using a double-stage approach, combining a silver-catalyzed alkyne/CO2 coupling and a subsequent base-catalyzed ring-expansion. This methodology avoids the formation of thermodynamically more stable, smaller-ring by-products and has good functional group tolerance. The synthetic application of these larger-ring cyclic carbonates is further demonstrated by showing their unique ability to serve as synthons for the preparation of bicyclic oxazolidinone pharmacores through an intramolecular domino sequence that involves a transient ketimine group, and various other intermolecular transformations. The results described herein significantly expand on the use of CO2 as a cheap and versatile carbon feedstock generating elusive heterocycles and pharmaceutically relevant compounds. Converting carbon dioxide (CO2) into valuable heterocycles is of great synthetic value but is usually limited to five- and six-membered ring compounds. Here, the authors report a catalytic approach for transforming this carbon renewable into seven-membered heterocycles, combining a silver-catalyzed alkyne/CO2 coupling and a subsequent base-catalyzed ring expansion.
Source: Nature Communications
Language: English
Subfield: Process Chemistry and Technology
Field: Chemical Engineering
Domain: Physical Sciences
SDG: Climate action
Open Access status: gold
Estimated APC paid: $6,990
OpenAlex ID: W4407159117