Photochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer
| dc.citation.articleNumber | 7881 | |
| dc.citation.journalTitle | Nature Communications | |
| dc.citation.volumeNumber | 13 | |
| dc.contributor.author | Bian, Kang-Jie | |
| dc.contributor.author | Kao, Shih-Chieh | |
| dc.contributor.author | Nemoto, David | |
| dc.contributor.author | Chen, Xiao-Wei | |
| dc.contributor.author | West, Julian G. | |
| dc.date.accessioned | 2023-01-27T14:47:35Z | |
| dc.date.available | 2023-01-27T14:47:35Z | |
| dc.date.issued | 2022 | |
| dc.description.abstract | Vicinal diamines are privileged synthetic motifs in chemistry due to their prevalence and powerful applications in bioactive molecules, pharmaceuticals, and ligand design for transition metals. With organic diazides being regarded as modular precursors to vicinal diamines, enormous efforts have been devoted to developing efficient strategies to access organic diazide generated from olefins, themselves common feedstock chemicals. However, state-of-the-art methods for alkene diazidation rely on the usage of corrosive and expensive oxidants or complicated electrochemical setups, significantly limiting the substrate tolerance and practicality of these methods on large scale. Toward overcoming these limitations, here we show a photochemical diazidation of alkenes via iron-mediated ligand-to-metal charge transfer (LMCT) and radical ligand transfer (RLT). Leveraging the merger of these two reaction manifolds, we utilize a stable, earth abundant, and inexpensive iron salt to function as both radical initiator and terminator. Mild conditions, broad alkene scope and amenability to continuous-flow chemistry rendering the transformation photocatalytic were demonstrated. Preliminary mechanistic studies support the radical nature of the cooperative process in the photochemical diazidation, revealing this approach to be a powerful means of olefin difunctionalization. | |
| dc.identifier.citation | Bian, Kang-Jie, Kao, Shih-Chieh, Nemoto, David, et al.. "Photochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer." <i>Nature Communications,</i> 13, (2022) Springer Nature: https://doi.org/10.1038/s41467-022-35560-3. | |
| dc.identifier.digital | s41467-022-35560-3 | |
| dc.identifier.doi | https://doi.org/10.1038/s41467-022-35560-3 | |
| dc.identifier.uri | https://hdl.handle.net/1911/114292 | |
| dc.language.iso | eng | |
| dc.publisher | Springer Nature | |
| dc.rights | This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. | |
| dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
| dc.title | Photochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer | |
| dc.type | Journal article | |
| dc.type.dcmi | Text | |
| dc.type.publication | publisher version |
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