Related Experiment Video
Updated: May 31, 2025
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Chiral Bis-8-Aryl-isoquinoline Bis-alkylamine Iron Catalysts for Asymmetric Oxidation Reactions
Tomer Mintz1, Lei Liu2, Doron Pappo1
1Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 8410501, Israel.
Abstract:
A novel class of bis-8-aryl-isoquinoline (iQ) bis-alkylamine iron complexes, FeII(iQ)(OTf)2 and FeII(iQ)(OTf)2 (dp = dipyrrolidinyl or mc = N,N'-dimethylcyclohexyl-diamine), for asymmetric oxidation reactions is reported. The scalable divergent synthesis of 8-aryl-3-formylisoquinolines (8), the key intermediates in preparing these ligands, enables precise structural and electronic tuning around the metal center. The enantioselective epoxidation and hydroxy carbonylation of conjugated alkenes, mediated by the FeII(iQ) catalyst with H2O2 as the oxidant, demonstrates the potential of these redox FeII[N4] catalysts in inducing face selection in oxygen transfer transformations.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
08:25Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
Published on: January 17, 2020
Related Concept Videos
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3