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 |
| Summary: | 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. |
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| ISSN: | 2399-3669 |