Chemoselective boronic ester synthesis via controlled speciation

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

Research output: Contribution to journalArticle

34 Citations (Scopus)

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.
LanguageEnglish
Pages12077–12080
Number of pages14
JournalAngewandte Chemie
Volume53
Issue number45
Early online date29 Sep 2014
DOIs
Publication statusPublished - 3 Nov 2014

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esters
Esters
Boronic Acids
synthesis
Oligomerization
acids
cross coupling
manipulators
catalysts
Catalysts

Keywords

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

Cite this

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
Fyfe, James W. B. ; Seath, Ciaran P. ; Watson, Allan J. B. / Chemoselective boronic ester synthesis via controlled speciation. In: Angewandte Chemie. 2014 ; Vol. 53, No. 45. pp. 12077–12080.
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Fyfe, JWB, Seath, CP & Watson, AJB 2014, 'Chemoselective boronic ester synthesis via controlled speciation' Angewandte Chemie, vol. 53, no. 45, pp. 12077–12080. https://doi.org/10.1002/anie.201406714

Chemoselective boronic ester synthesis via controlled speciation. / Fyfe, James W. B.; Seath, Ciaran P.; Watson, Allan J. B.

In: Angewandte Chemie, Vol. 53, No. 45, 03.11.2014, p. 12077–12080.

Research output: Contribution to journalArticle

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AU - Seath, Ciaran P.

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AB - 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.

KW - chemoselectivity

KW - boron

KW - boronic acid solution speciation

KW - cross-coupling

KW - palladium

KW - boronic ester

KW - oligomerization

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