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Oxenoid Reactivity Enabled by Targeted Photoactivation of Periodate. | LitMetric

Oxenoid Reactivity Enabled by Targeted Photoactivation of Periodate.

Angew Chem Int Ed Engl

Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, U.K.

Published: October 2024

AI Article Synopsis

  • * Researchers used violet-light photolysis of tetrabutylammonium periodate to generate oxene, showing how this method allows for effective reactivity and functional group compatibility.
  • * This novel approach opens new pathways for the application of oxene in organic synthesis, potentially leading to innovative oxygen-based reactions in both industrial and academic settings.

Article Abstract

The chemistry of low-valent intermediates continues to inspire new modes of reactivity across synthetic chemistry. But while the generation and reactivity of both carbenes and nitrenes are well-established, difficulties in accessing oxene, their oxygen-based congener, has severely hampered its application in synthesis. Here, we report a conceptually novel approach towards oxenoid reactivity through the violet-light photolysis of tetrabutylammonium periodate. Computational studies reveal an unexpected geometric change upon periodate photoexcitation that facilitates intersystem crossing and near-barrierless dissociation of triplet periodate into oxene. Under these operationally simple conditions, we have demonstrated the epoxidation of a wide range of substituted olefins, revealing unprecedented functional group compatibility. By overcoming the historic challenges associated with employing oxene as an intermediate in organic chemistry, we believe that this platform will inspire the development of new reactive oxygen-based methodologies across industry and academia.

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Source
http://dx.doi.org/10.1002/anie.202417402DOI Listing

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