Carbonyl-to-nickel exchange on a lactam skeleton
Molecular skeletal editing has a wide range of applications in late-stage derivatization, but metal–carbon exchange is underexplored due to the challenges in selectively cleaving highly inert chemical bonds and forming stable intermediates. Here, skeletal metalation of lactams enables a carbonyl-to-...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-10-01
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| Series: | Communications Chemistry |
| Online Access: | https://doi.org/10.1038/s42004-023-01022-0 |
| _version_ | 1797577562587660288 |
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| author | Huijuan Guo |
| author_facet | Huijuan Guo |
| author_sort | Huijuan Guo |
| collection | DOAJ |
| description | Molecular skeletal editing has a wide range of applications in late-stage derivatization, but metal–carbon exchange is underexplored due to the challenges in selectively cleaving highly inert chemical bonds and forming stable intermediates. Here, skeletal metalation of lactams enables a carbonyl-to-nickel exchange via Ni(0) reagent-mediated selective C–N bond oxidative addition and decarbonylation, generating synthetically useful organonickel reagents for the deletion and exchange of single atoms in the lactam core. |
| first_indexed | 2024-03-10T22:10:06Z |
| format | Article |
| id | doaj.art-31e09cc76a594319a866f60573865eb5 |
| institution | Directory Open Access Journal |
| issn | 2399-3669 |
| language | English |
| last_indexed | 2024-03-10T22:10:06Z |
| publishDate | 2023-10-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Communications Chemistry |
| spelling | doaj.art-31e09cc76a594319a866f60573865eb52023-11-19T12:37:26ZengNature PortfolioCommunications Chemistry2399-36692023-10-01611210.1038/s42004-023-01022-0Carbonyl-to-nickel exchange on a lactam skeletonHuijuan Guo0Communications ChemistryMolecular skeletal editing has a wide range of applications in late-stage derivatization, but metal–carbon exchange is underexplored due to the challenges in selectively cleaving highly inert chemical bonds and forming stable intermediates. Here, skeletal metalation of lactams enables a carbonyl-to-nickel exchange via Ni(0) reagent-mediated selective C–N bond oxidative addition and decarbonylation, generating synthetically useful organonickel reagents for the deletion and exchange of single atoms in the lactam core.https://doi.org/10.1038/s42004-023-01022-0 |
| spellingShingle | Huijuan Guo Carbonyl-to-nickel exchange on a lactam skeleton Communications Chemistry |
| title | Carbonyl-to-nickel exchange on a lactam skeleton |
| title_full | Carbonyl-to-nickel exchange on a lactam skeleton |
| title_fullStr | Carbonyl-to-nickel exchange on a lactam skeleton |
| title_full_unstemmed | Carbonyl-to-nickel exchange on a lactam skeleton |
| title_short | Carbonyl-to-nickel exchange on a lactam skeleton |
| title_sort | carbonyl to nickel exchange on a lactam skeleton |
| url | https://doi.org/10.1038/s42004-023-01022-0 |
| work_keys_str_mv | AT huijuanguo carbonyltonickelexchangeonalactamskeleton |