Chemoselective boronic ester synthesis via controlled speciation

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

Research output: Contribution to journalArticlepeer-review

41 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.
Original languageEnglish
Pages (from-to)12077-12080
Number of pages4
JournalAngewandte Chemie International Edition
Volume53
Issue number45
DOIs
Publication statusPublished - 3 Nov 2014

Keywords

  • Chemoselectivity
  • Boron
  • Boronic acid solution speciation
  • Cross-coupling
  • Palladium
  • Boronic ester
  • Oligomerization

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