Improved method for the conversion of pinacolboronic esters into trifluoroborate salts: facile synthesis of chiral secondary and tertiary trifluoroborates

Viktor Bahutski, Abel Ros Lao, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

72 Citations (Scopus)

Abstract

A general method for the preparation of virtually any potassium trifluoroborate salt from the corresponding pinacolboronic ester is reported. Thus, conditions for an azeotropic removal of pinacol from the reaction mixture were found to afford the desired potassium trifluoroborates Of Sufficient purity (>95%) in nearly quantitative yields irrespective of the nature of the product. The utility of this method is illustrated by the preparation of a broad range of enantioenriched secondary and tertiary potassium trifluoroborates. (C) 2009 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)9956-9960
Number of pages5
JournalTetrahedron
Volume65
Issue number48
DOIs
Publication statusPublished - 28 Nov 2009

Keywords

  • CROSS-COUPLING REACTIONS
  • EXPANDING ORGANOBORON CHEMISTRY
  • RHODIUM-CATALYZED ADDITION
  • POTASSIUM
  • ENONES
  • ARYL
  • PALLADIUM
  • PERSPECTIVES
  • ALDEHYDES
  • PARTNERS

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