Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Design of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Ketones

Version 1 : Received: 24 April 2021 / Approved: 26 April 2021 / Online: 26 April 2021 (14:16:15 CEST)

A peer-reviewed article of this Preprint also exists.

Bernier, C.M.; Merola, J.S. Design of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Aryl Ketones. Catalysts 2021, 11, 671. Bernier, C.M.; Merola, J.S. Design of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Aryl Ketones. Catalysts 2021, 11, 671.

Journal reference: Catalysts 2021, 11, 671
DOI: 10.3390/catal11060671

Abstract

A series of chiral complexes of the form Ir(NHC)2(aa)(H)(X) (NHC = N-heterocyclic carbene, aa = chelated amino acid, X = halide) was synthesized by oxidative addition of -amino acids to iridium(I) bis-NHC compounds and screened for asymmetric transfer hydrogenation of ketones. Following optimization of the reaction conditions, NHC, and amino acid ligands, high enantioselectivity was achieved when employing the Ir(IMe)2(l-Pro)(H)(I) catalyst (IMe = 1,3-dimethylimidazol-2-ylidene), which asymmetrically reduces a range of acetophenone derivatives in up to 95% enantiomeric excess.

Keywords

iridium; N-heterocyclic carbene; amino acid; asymmetric transfer hydrogenation

Subject

CHEMISTRY, Analytical Chemistry

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