Mild and Efficient Synthesis of Diverse Organo-Au(I)-L Complexes in Green Solvents

Fredric J. L Inger, Ann-Catherin Schmitt, Andreas Orthaber, Paul J Gates, Lukasz T Pilarski

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

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Abstract

An exceptionally mild and efficient method is presented for the preparation of (hetero)aryl-AuI-L complexes using ethanol or water as the reaction medium at room temperature and R-B(triol)K boronates as the transmetalation partner. The reaction returns up to quantitative yields, needs no exogeneous base or other additives and a simple filtration is the only required purification method, which
obviates considerable waste associated with alternative workup methods. A broad reaction scope is demonstrated with respect to both the L and (hetero)aryl ligands on product Au complexes. Despite the polar reaction medium, large polycyclic aromatic hydrocarbon units can be incorporated on the product Au complexes in very good to excellent yields. We demonstrate the use of our approach for the
chemoselective manipulation of orthogonally protected aryl boronates to afford a novel new class of NHC-Au-aryl complexes. A mechanistic rationale is proposed.
Original languageEnglish
Pages (from-to)2032-2037
Number of pages6
JournalChemSusChem
Volume13
Issue number8
Early online date3 Mar 2020
DOIs
Publication statusPublished - 20 Apr 2020

Keywords

  • green solvents
  • gold
  • boronates
  • NHC
  • synthesis

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