Phosphinine-Based Ligands in Gold-Catalyzed Reactions

Massimo Rigo, Evi R.M. Habraken, Koyel Bhattacharyya, Manuela Weber, Andreas W. Ehlers, Nicolas Mézailles, J. Chris Slootweg, Christian Müller*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

A series of substituted phosphinines, 1-phosphabarrelenes and 5-phosphasemibullvalenes were synthesized and evaluated for their potential application as ligands in homogeneous catalytic reactions. While their buried volume (%Vbur) was calculated to get insight into the steric properties, [LNi(CO)3] complexes were prepared in order to determine the corresponding Tolman electronic parameter. ETS-NOCV (extended-transition-state natural orbital for chemical valence) calculations on [LAuCl] complexes further allowed an estimation of the σ- and π-contributions to the L−M interaction. AuI coordination compounds of selected examples were prepared and characterized by single crystal X-ray diffraction. Finally, the three classes of PIII compounds were successfully used in the AuI-catalyzed cycloisomerization of N-2-propyn-1-ylbenzamide, showing very good activities and selectivities, which are comparable with the reported data of cationic phosphorus-based gold catalysts.

Original languageEnglish
Pages (from-to)8769-8779
Number of pages11
JournalChemistry - A European Journal
Volume25
Issue number37
DOIs
Publication statusPublished - 2 Jul 2019
Externally publishedYes

Keywords

  • density functional calculations
  • heterocycles
  • homogeneous gold catalysis
  • phosphorus ligands
  • X-ray diffraction

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