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

Csilla Enik Czégéni, Gábor Papp, A. Kathó, Ferenc Joó

Research output: Contribution to journalArticle

52 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

Fingerprint

Alkynes
alkynes
Gold
Hydration
hydration
catalytic activity
Catalyst activity
carbenes
gold
catalysts
Catalysts
Water
water
chlorides
Sulfonation
Methanol
Chlorides
methyl alcohol
Chemical activation
Ligands

Keywords

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

ASJC Scopus subject areas

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

Cite this

Water-soluble gold(I)-NHC complexes of sulfonated IMes and SIMes and their catalytic activity in hydration of alkynes. / Czégéni, Csilla Enik; Papp, Gábor; Kathó, A.; Joó, Ferenc.

In: Journal of Molecular Catalysis A: Chemical, Vol. 340, No. 1-2, 23.04.2011, p. 1-8.

Research output: Contribution to journalArticle

@article{25e5ca6d382e45499aca4ec2f3259303,
title = "Water-soluble gold(I)-NHC complexes of sulfonated IMes and SIMes and their catalytic activity in hydration of alkynes",
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.",
keywords = "Alkynes, Gold(I)-NHC complexes, Hydration, IMes, SIMes, Water-soluble catalysts",
author = "Cz{\'e}g{\'e}ni, {Csilla Enik} and G{\'a}bor Papp and A. Kath{\'o} and Ferenc Jo{\'o}",
year = "2011",
month = "4",
day = "23",
doi = "10.1016/j.molcata.2011.03.009",
language = "English",
volume = "340",
pages = "1--8",
journal = "Journal of Molecular Catalysis A: Chemical",
issn = "1381-1169",
publisher = "Elsevier",
number = "1-2",

}

TY - JOUR

T1 - Water-soluble gold(I)-NHC complexes of sulfonated IMes and SIMes and their catalytic activity in hydration of alkynes

AU - Czégéni, Csilla Enik

AU - Papp, Gábor

AU - Kathó, A.

AU - Joó, Ferenc

PY - 2011/4/23

Y1 - 2011/4/23

N2 - 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.

AB - 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.

KW - Alkynes

KW - Gold(I)-NHC complexes

KW - Hydration

KW - IMes

KW - SIMes

KW - Water-soluble catalysts

UR - http://www.scopus.com/inward/record.url?scp=79955634878&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79955634878&partnerID=8YFLogxK

U2 - 10.1016/j.molcata.2011.03.009

DO - 10.1016/j.molcata.2011.03.009

M3 - Article

AN - SCOPUS:79955634878

VL - 340

SP - 1

EP - 8

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

SN - 1381-1169

IS - 1-2

ER -