Chemoselective boronic ester synthesis via controlled speciation

James W. B. Fyfe, Ciaran P. Seath, Allan J. B. Watson

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Abstract

Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active Pd catalyst also facilitates streamlined iterative catalytic C-C bond formation and provides a method for the controlled oligomerization of sp2-hybridized boronic esters.
Original languageEnglish
Pages (from-to)12077–12080
Number of pages14
JournalAngewandte Chemie
Volume53
Issue number45
Early online date29 Sep 2014
DOIs
Publication statusPublished - 3 Nov 2014

Keywords

  • chemoselectivity
  • boron
  • boronic acid solution speciation
  • cross-coupling
  • palladium
  • boronic ester
  • oligomerization

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    Fyfe, J. W. B., Seath, C. P., & Watson, A. J. B. (2014). Chemoselective boronic ester synthesis via controlled speciation. Angewandte Chemie, 53(45), 12077–12080. https://doi.org/10.1002/anie.201406714