Related Experiment Video
Updated: Jan 18, 2026
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Theoretical Study of Ru-Catalyzed Decarboxylative Heteroarylation of Aryl Carboxylic Acids
Wei Li1, Zhewei Li1, Shuo Zhang1
1State Key Laboratory of Chemical Resource Engineering, Institute of Computational Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.
Abstract:
The ortho-di(2-pyridyl)arenes, featuring a unique structure, hold significant promise for applications in fluorescent probes, synthetic nanoparticle stabilizers, and chemical synthesis. The mechanism of Ru-catalyzed decarboxylation and heteroarylation reactions of aryl carboxylic acids to access ortho-dipyridylarenes was elucidated using DFT calculations, which involved C-H bond activation, oxidative addition, reductive elimination, and decarboxylation processes to form ortho-di(2-pyridyl)arenes. The rate-determining step of the reaction is the second reductive elimination step with an energy barrier of 27.1 kcal/mol. The calculated results indicated that the ligand 1,10-phenanthroline will promote the first C-C coupling process and inhibit the second C-C coupling process, while the aryl carboxylic acids will promote the second C-C coupling reaction. In addition, the origin of selectively generating ortho-di(2-pyridyl)arenes was revealed due to the high energy barrier of forming ortho-tri(3-pyridyl)arenes. These insights aid in optimizing reaction conditions and designing efficient catalytic processes for the synthesis of ortho-di(2-pyridyl)arenes.
More Related Videos
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
10:39Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
Published on: August 23, 2018
Related Concept Videos
01:13Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
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 stereochemistry.
01:15α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
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...
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration