Ligand scaffold optimization of a supramolecular hydrogenation catalyst: Analyzing the influence of key structural subunits on reactivity and selectivity

Nathan C. Thacker, Shin A. Moteki, James M. Takacs

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Results are reported for the catalytic asymmetric hydrogenation of two prototypical substrates with a series of more than 150 closely related supramolecular catalysts differing in only their ligand/catalyst scaffold. These modular catalysts are constructed from four subunits and vary widely in their reactivity (no reaction to quantitative yield) and enantioselectivity (racemic to 96% enantiomeric excess (ee)). Analysis of the ligand/catalyst scaffold optimization data reveals how each subunit contributes to the effectiveness of the modular supramolecular catalyst. The results suggest that a balance between key elements of rigidity and flexibility is required for the successful catalysts and, moreover, that this balance is required to enable effective fine-tuning via catalyst scaffold optimization.

Original languageEnglish (US)
Pages (from-to)2743-2752
Number of pages10
JournalACS Catalysis
Volume2
Issue number12
DOIs
StatePublished - Dec 7 2012

Keywords

  • asymmetric catalysis
  • asymmetric hydrogentaion
  • rhodium-catalyzed
  • self-assembled ligands
  • self-assembly
  • supramolecular catalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Ligand scaffold optimization of a supramolecular hydrogenation catalyst: Analyzing the influence of key structural subunits on reactivity and selectivity'. Together they form a unique fingerprint.

  • Cite this