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Issue 5, 2017
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Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids

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Abstract

Unprecedented palladium-catalyzed denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids have been realized, which afforded structurally diverse ortho-amino-substituted biaryl and biaryl ketone derivatives. The key to this success is due to the development of a rationally designed strategy to achieve the ring opening of benzotriazoles with a synergistic activating–stabilizing effect, which enables the in situ generation of the corresponding ortho-amino-arenediazonium species. The present work opens up a new avenue to utilize benzotriazoles as synthetic equivalents of ortho-amino-arenediazoniums, which otherwise could not be directly accessed by existing synthetic methods.

Graphical abstract: Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids

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Publication details

The article was received on 24 Jan 2017, accepted on 10 Mar 2017 and first published on 15 Mar 2017


Article type: Edge Article
DOI: 10.1039/C7SC00367F
Citation: Chem. Sci., 2017,8, 3852-3857
  • Open access: Creative Commons BY license
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    Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids

    Y. Wang, Y. Wu, Y. Li and Y. Tang, Chem. Sci., 2017, 8, 3852
    DOI: 10.1039/C7SC00367F

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