Photochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer

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dc.citation.articleNumber7881en_US
dc.citation.journalTitleNature Communicationsen_US
dc.citation.volumeNumber13en_US
dc.contributor.authorBian, Kang-Jieen_US
dc.contributor.authorKao, Shih-Chiehen_US
dc.contributor.authorNemoto, Daviden_US
dc.contributor.authorChen, Xiao-Weien_US
dc.contributor.authorWest, Julian G.en_US
dc.date.accessioned2023-01-27T14:47:35Zen_US
dc.date.available2023-01-27T14:47:35Zen_US
dc.date.issued2022en_US
dc.description.abstractVicinal 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.en_US
dc.identifier.citationBian, 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.en_US
dc.identifier.digitals41467-022-35560-3en_US
dc.identifier.doihttps://doi.org/10.1038/s41467-022-35560-3en_US
dc.identifier.urihttps://hdl.handle.net/1911/114292en_US
dc.language.isoengen_US
dc.publisherSpringer Natureen_US
dc.rightsThis 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.en_US
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/en_US
dc.titlePhotochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transferen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpublisher versionen_US
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