Development of Ferrocene-Based Planar Chiral Imidazopyridinium
Salts for Catalysis
Posted on 2020-06-30 - 16:23
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 π acidity 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.
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Fitzpatrick, Keegan
P.; Schwamb, C. Benjamin; Check, Christopher T.; Jang, Ki-Po; Barsoum, David N.; Scheidt, Karl A. (2020). Development of Ferrocene-Based Planar Chiral Imidazopyridinium
Salts for Catalysis. ACS Publications. Collection. https://doi.org/10.1021/acs.organomet.0c00312