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Mechanistic examination of AuIII-mediated 1,5-enyne cycloisomerization by AuBr2(N-imidate)(NHC) / AgX precatalysts - is the active catalyst AuIII or AuI?

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JournalCatalysis Science and Technology
DateAccepted/In press - 2014
DateE-pub ahead of print (current) - 24 Jul 2014
Volume4
Number of pages10
Pages (from-to)3524-3533
Early online date24/07/14
Original languageEnglish

Abstract

Gold(III) catalysts mediate 1,5-enyne cycloisomerization or tandem nucleophilic substitution-1,5-enyne cycloisomerization processes in an efficient manner. This study examines the reaction kinetics of 1,5-enyne cycloisomerization, mediated by AuBr2(N-imidate)(NHC) catalysts {where N-imidate = N-tetrafluorosuccinimide (N-TFS) or N-phthalimide (N-phthal) and NHC = N,N′-di-tert-pentylimidazol-2-ylidene (ItPe)}, in the presence of AgOTf, in comparison with AuIIIBr3(NHC) and AuIBr(NHC). The nature of N-imidate anion influences catalyst efficacy. NMR spectroscopic investigations have allowed the ease of reduction of AuBr2(N-TFS)(NHC) to AuIX(NHC) (where X = N-TFS or Br) to be examined. Br2 is liberated from AuIII, which has been trapped by a sacrificial alkene. Under working catalyst conditions cationic AuIII is reduced to AuI.

    Research areas

  • GOLD CATALYSIS, CATALYSIS, KINETICS, MECHANISM, ENYNE CYCLOISOMERIZATIONS, NMR, GOLD CATALYSTS

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