Synthesis of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity

Janssens, Julien;Berionni, Guillaume;Robiette, Raphaël
(2025) European Journal of Organic Chemistry — Vol. 28, p. e202500033 (2025)

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Authors
  • Janssens, JulienUCLouvain
    Author
  • Berionni, Guillaumeorcid-logoUNamur
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  • Robiette, Raphaëlorcid-logoUCLouvain
    Author
Abstract
We have investigated the possibility of synthesizing substituted vinyl boronates from gem-borylsilylmethane derivatives using the Peterson olefination. Our results show a total chemoselectivity for the Peterson olefination over the boron-Wittig reaction, and a low Z selectivity, regardless of the nature of the carbonyl partner. A mechanistic study helps explain observed reactivity, chemoselectivity and stereoselectivity.
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Janssens, J., Berionni, G., & Robiette, R. (2025). Synthesis of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity. European Journal of Organic Chemistry, 28, e202500033. https://doi.org/10.1002/ejoc.202500033 (Original work published 2025)