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Unveiling the role of boroxines in metal-free carbon–carbon homologations using diazo compounds and boronic acids

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Abstract

By means of computational and experimental mechanistic studies the fundamental role of boroxines in the reaction between diazo compounds and boronic acids was elucidated. Consequently, a selective metal-free carbon–carbon homologation of aryl and vinyl boroxines using TMSCHN2, giving access to TMS-pinacol boronic ester products, was developed.

Graphical abstract: Unveiling the role of boroxines in metal-free carbon–carbon homologations using diazo compounds and boronic acids

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Publication details

The article was received on 19 May 2017, accepted on 15 Jun 2017 and first published on 15 Jun 2017


Article type: Edge Article
DOI: 10.1039/C7SC02264F
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Unveiling the role of boroxines in metal-free carbon–carbon homologations using diazo compounds and boronic acids

    C. Bomio, M. A. Kabeshov, A. R. Lit, S. Lau, J. Ehlert, C. Battilocchio and S. V. Ley, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC02264F

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