Balancing bulkiness in gold(I) phosphino-triazole catalysis

Research output: Contribution to journalArticlepeer-review

Authors

  • Yiming Zhao
  • Mat Wakeling
  • Fernanda Meloni
  • TJ Sum
  • Benjamin R Buckley

Colleges, School and Institutes

External organisations

  • Loughborough University

Abstract

The syntheses of a series of 1-phenyl-5-phosphino1,2,3-triazoles are disclosed, within which, the phosphorus atom(at the 5-position of a triazole) is appended by one, two or three triazole motifs, and the valency of the phosphorus(III) atom is completed by two, one or zero ancillary (phenyl or cyclohexyl) groups respectively. This series of phosphines was compared with tricyclohexylphosphine and triphenylphosphine to study the effect of increasing the number of triazoles appended to the central phosphorus atom from zero to three triazoles. Gold(I) chloride complexes of the synthesised ligands were prepared and analysed by techniques including single-crystal X-ray diffraction structure determination. Gold(I) complexes were also prepared from 1-(2,6-dimethoxy)-phenyl-5-dicyclohexyl-phos-phino 1,2,3-triazole and 1-(2,6-dimethoxy)-phenyl-5-diphenyl-phosphino 1,2,3-triazole ligands. The crystal structures thus obtained were examined using the SambVca (2.0)web tool and percentage buried volumes determined. The effectiveness of these gold(I) chloride complexes to serve as precatalysts for alkyne hydration were assessed. Furthermore, the regioselectivity of hydration of but-1-yne-1,4-diyldibenzene was probed.

Details

Original languageEnglish
Pages (from-to)5540-5548
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number31-32
Early online date30 Jul 2019
Publication statusPublished - 1 Sep 2019

Keywords

  • Click chemistry, Gold, Homogeneous catalysis, Phosphane ligands, Triazoles