Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones

Wangyu Shi, Jordi Benet-Buchholz and Arjan W. Kleij ()
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Wangyu Shi: Institute of Chemical Research of Catalonia (ICIQ-Cerca)
Jordi Benet-Buchholz: Institute of Chemical Research of Catalonia (ICIQ-Cerca)
Arjan W. Kleij: Institute of Chemical Research of Catalonia (ICIQ-Cerca)

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: 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.

Date: 2025
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DOI: 10.1038/s41467-025-56681-5

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