Development of Ferrocene-Based Planar Chiral Imidazopyridinium Salts for Catalysis

Keegan P. Fitzpatrick, C. Benjamin Schwamb, Christopher T. Check, Ki Po Jang, David N. Barsoum, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Imidazol-2-ylidenes and their N,N′-diaryl derivatives constitute an important class of N-heterocyclic carbenes (NHCs) which possess a unique level of versatility in both organocatalysis and transition-metal catalysis. However, there remain few examples of carbenes of this type that are chiral. Here we describe the development of a family of closely related imidazopyridine-based NHCs that derive their asymmetry purely from planar chirality through the incorporation of the classic metallocene framework. An NMR analysis of 77Se complexes of this family is used to assess their degrees of σ donicity and πacidity in comparison to a larger family of NHCs. Percent buried volume (%Vbur) calculations were performed to measure the steric bulk of this distinct class of NHCs. Additionally, these NHCs were employed in various enantioselective transformations to survey their use as organocatalysts as well as ligands for transition-metal-catalyzed processes.

Original languageEnglish (US)
Pages (from-to)2705-2712
Number of pages8
JournalOrganometallics
Volume39
Issue number14
DOIs
StatePublished - Jul 27 2020

Funding

Financial support was generously provided by the NSF (CHE-1665141; CHE-1152010). The authors also thank Charlotte Stern from the Integrated Molecular Structure Education and Research Center (IMSERC) at Northwestern University for assistance with X-ray crystallography.

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint

Dive into the research topics of 'Development of Ferrocene-Based Planar Chiral Imidazopyridinium Salts for Catalysis'. Together they form a unique fingerprint.

Cite this