Ph3PCN2: a stable reagent for carbon atom transfer
| dc.contributor.author | Koike, Taichi | |
| dc.contributor.author | Yu, Jhen-Kuei | |
| dc.contributor.author | Hansmann, Max M. | |
| dc.date.accessioned | 2024-07-19T11:38:40Z | |
| dc.date.available | 2024-07-19T11:38:40Z | |
| dc.date.issued | 2024-07-18 | |
| dc.description.abstract | Precise modification of a chemical site in a molecule at the single-atom level is one of the most elegant yet difficult transformations in chemistry. A reagent specifically designed for chemoselective introduction of monoatomic carbon is a particularly formidable challenge. Here we report a straightforward, azide-free synthesis of a crystalline and isolable diazophosphorus ylide Ph3PCN2, a stable compound with a carbon atom bonded to two chemically labile groups, triphenylphosphine (PPh3) and dinitrogen (N2). Without any additives, the diazophosphorus ylide serves as a highly selective transfer reagent for fragments including Ph3PC to deliver phosphorus ylide-terminated heterocumulenes and CN2 to produce multi-substituted pyrazoles. Ultimately, even exclusive C-atom transfer is possible: In reactions with aldehydes, acyclic and cyclic ketones (R2C=O), the C-atom substitution forms a vinylidene (R2C=C:) en route to alkynes or butatrienes. | en |
| dc.identifier.uri | http://hdl.handle.net/2003/42605 | |
| dc.identifier.uri | http://dx.doi.org/10.17877/DE290R-24440 | |
| dc.language.iso | en | de |
| dc.relation.ispartofseries | Science;385(6706) | |
| dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | de |
| dc.subject.ddc | 540 | |
| dc.title | Ph3PCN2: a stable reagent for carbon atom transfer | en |
| dc.type | Text | de |
| dc.type.publicationtype | ResearchArticle | de |
| dcterms.accessRights | open access | |
| eldorado.secondarypublication | true | de |
| eldorado.secondarypublication.primarycitation | Taichi Koike et al., Ph3PCN2: A stable reagent for carbon-atom transfer. Science 385, 305-311 (2024). DOI: 10.1126/science.ado4564 | de |
| eldorado.secondarypublication.primaryidentifier | https://doi.org/10.1126/science.ado4564 | de |