The gold(I)-catalysed protodecarboxylation mechanism

Stephanie Dupuy, Luke Crawford, Michael Buehl, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)
2 Downloads (Pure)

Abstract

A mechanistic study of the gold-catalysed protodecarboxylation is described. Each reaction step has been investigated experimentally and computationally. More specifically, the activation parameters for the decarboxylation step have been determined through kinetic studies. Further experimental studies on the hydrolysis of the arylgold intermediate have revealed that the protodeauration can become competitive with the decarboxylation process at high conversions. This switch in rate-limiting step has been shown to be pKa-dependent. These studies have been supported by DFT calculations and permit a better understanding of which prevalent features of the reaction mechanism account for the decarboxylation process.
Original languageEnglish
Pages (from-to)3399-3408
JournalChemistry - A European Journal
Volume21
Issue number8
Early online date7 Jan 2015
DOIs
Publication statusPublished - 16 Feb 2015

Keywords

  • Decarboxylation
  • Gold
  • Mechanism
  • N-heterocycle carbenes
  • Protodeauration

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