Mechanism of Au(III)-Mediated Alkoxycyclization of a 1,6-Enyne

Ann Christin Reiersølmoen, Dániel Csókás, Imre Pápai, Anne Fiksdahl, Máté Erdélyi

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2 Citations (Scopus)

Abstract

Gold-mediated homogeneous catalysis is a powerful tool for construction of valuable molecules and has lately received growing attention. Whereas Au(I)-catalyzed processes have become well established, those mediated by Au(III) have so far barely been explored, and their mechanistic understanding remains basic. Herein, we disclose the combined NMR spectroscopic, single-crystal X-ray crystallographic, and computational (DFT) investigation of the Au(III)-mediated alkoxycyclization of a 1,6-enyne in the presence of a bidentate pyridine-oxazoline ligand. The roles of the counterion, the solvent, and the type of Au(III) complex have been assessed. Au(III) is demonstrated to be the active catalyst in alkoxycyclization. Alkyne coordination to Au(III) involves decoordination of the pyridine nitrogen and is the rate-limiting step.

Original languageEnglish
Pages (from-to)18221-18229
Number of pages9
JournalJournal of the American Chemical Society
Volume141
Issue number45
DOIs
Publication statusPublished - Jan 1 2019

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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