2012/01/30 by Markus J. Spallek, Dominic Riedel, Frank Rominger +3 · 1 citation
Chemistry · #Catalytic Cross-Coupling Reactions #N-Heterocyclic Carbenes in Organic and Inorganic Chemistry #Organoboron and organosilicon chemistry
paper · doi:10.1021/om201166b
openalex publication_date 2012/01/30 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28
A series of three chiral, expanded six-membered NHC–palladium(II) complexes was prepared with successively increased sterical demand, while retaining natural d -(+)-camphor as a chiral motif. The catalysts showed different reaction profiles in the asymmetric, intramolecular α-arylation of amides. The molecular structure of two N - heterocyclic and one nitrogen acyclic carbene palladium isonitrile complex was unequivocally determined by X-ray crystallographic analysis. The results reported herein account for a correlation of catalytic activity and enantiodiscrimination in relation to the degree of chiral substitution and steric congestion at the metal center. The modular and convergent synthetic route of these air- and moisture-stable palladium isonitrile complexes underlines the usefulness of this approach.