1. Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones.
- Author
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Shi, Wangyu, Benet-Buchholz, Jordi, and Kleij, Arjan W.
- Abstract
Converting carbon dioxide (CO
2 ) 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. [ABSTRACT FROM AUTHOR]- Published
- 2025
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