Authors: | Koike, Taichi Yu, Jhen-Kuei Hansmann, Max M. |
Title: | Ph3PCN2: a stable reagent for carbon atom transfer |
Language (ISO): | en |
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. |
URI: | http://hdl.handle.net/2003/42605 http://dx.doi.org/10.17877/DE290R-24440 |
Issue Date: | 2024-07-18 |
Rights link: | https://creativecommons.org/licenses/by/4.0/ |
Appears in Collections: | Organische Chemie |
Files in This Item:
File | Description | Size | Format | |
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accepted_manuscript.pdf | DNB | 1.48 MB | Adobe PDF | View/Open |
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