Water-soluble gold(I)-NHC complexes of sulfonated IMes and SIMes and their catalytic activity in hydration of alkynes

Csilla Enik Czégéni, Gábor Papp, Ágnes Kathó, Ferenc Joó

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

The water-soluble carbene ligand precursors sIMesH+Cl - and sSIMesH+Cl- were synthesized in high yields by direct sulfonation of IMesH+Cl- (1,3-bis(2,4,6-trimethylphenyl) imidazolium chloride) and SIMesH +Cl- (1,3-bis(2,4,6-trimethylphenyl)imidazolinium chloride). Gold(I)-N-heterocyclic carbene complexes [AuCl(sIMes)] and [AuCl(sSIMes)] were prepared by carbene transfer from the zwitterionic [Ag(sIMes)2] and [Ag(sSIMes)2] to [AuCl(tht)] (tht = tetrahydrothiophene). In methanol-water mixtures or in neat water, the new gold(I)-NHC complexes showed high catalytic activity in Markovnikov type hydration of terminal alkynes (up to a turnover frequency 1990 h-1; ethynyltoluene, 0.1 mol% catalyst) but were markedly less active in case of internal alkynes (TOF = 3.6 h-1; diphenylethyne, 1 mol% catalyst). These new Au(I)-NHC catalysts do not require acid co-catalysts or activation by Ag(I)-additives.

Original languageEnglish
Pages (from-to)1-8
Number of pages8
JournalJournal of Molecular Catalysis A: Chemical
Volume340
Issue number1-2
DOIs
Publication statusPublished - Apr 23 2011

Keywords

  • Alkynes
  • Gold(I)-NHC complexes
  • Hydration
  • IMes
  • SIMes
  • Water-soluble catalysts

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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