A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl-Alkyl Cross-Coupling Reactions.
Poh, Jian Siang
Blakemore, David C
Angewandte Chemie (International ed. in English)
John Wiley & Sons Ltd.
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Greb, A., Poh, J. S., Greed, S., Battilocchio, C., Pasau, P., Blakemore, D. C., & Ley, S. (2017). A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl-Alkyl Cross-Coupling Reactions.. Angewandte Chemie (International ed. in English), 56 (52), 16602-16605. https://doi.org/10.1002/anie.201710445
Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon-carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp2)-C(sp3) cross-coupling processes, with excellent functional group tolerance.
Pfizer The Cambridge Home and EU Scholarship Scheme UCB Biopharma SPRL
European Commission Horizon 2020 (H2020) Future and Emerging Technologies (FET) (737266)
External DOI: https://doi.org/10.1002/anie.201710445
This record's URL: https://www.repository.cam.ac.uk/handle/1810/276770
Attribution 4.0 International
Licence URL: http://creativecommons.org/licenses/by/4.0/
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