Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones
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,...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-02-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-56681-5 |
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| author | Wangyu Shi Jordi Benet-Buchholz Arjan W. Kleij |
| author_facet | Wangyu Shi Jordi Benet-Buchholz Arjan W. Kleij |
| author_sort | Wangyu Shi |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-ffbc4ff7c8dd43378a3b039111253f14 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-ffbc4ff7c8dd43378a3b039111253f142025-02-09T12:44:57ZengNature PortfolioNature Communications2041-17232025-02-0116111110.1038/s41467-025-56681-5Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinonesWangyu Shi0Jordi Benet-Buchholz1Arjan W. Kleij2Institute of Chemical Research of Catalonia (ICIQ-Cerca)Institute of Chemical Research of Catalonia (ICIQ-Cerca)Institute of Chemical Research of Catalonia (ICIQ-Cerca)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.https://doi.org/10.1038/s41467-025-56681-5 |
| spellingShingle | Wangyu Shi Jordi Benet-Buchholz Arjan W. Kleij Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones Nature Communications |
| title | Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones |
| title_full | Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones |
| title_fullStr | Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones |
| title_full_unstemmed | Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones |
| title_short | Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones |
| title_sort | catalytic transformation of carbon dioxide into seven membered heterocycles and their domino transformation into bicyclic oxazolidinones |
| url | https://doi.org/10.1038/s41467-025-56681-5 |
| work_keys_str_mv | AT wangyushi catalytictransformationofcarbondioxideintosevenmemberedheterocyclesandtheirdominotransformationintobicyclicoxazolidinones AT jordibenetbuchholz catalytictransformationofcarbondioxideintosevenmemberedheterocyclesandtheirdominotransformationintobicyclicoxazolidinones AT arjanwkleij catalytictransformationofcarbondioxideintosevenmemberedheterocyclesandtheirdominotransformationintobicyclicoxazolidinones |