AI Article Synopsis
- * This is the first time Wacker-type oxidation has been applied to trisubstituted alkenes and the process does not require transition metals, making it versatile across different functional groups.
- * The reaction occurs under mild conditions and produces good yields, with the mechanism involving a C=O bond formation through interactions between carbon cations and superoxide radicals, aided by a 1,2-shift of an electron-rich substituent.
Article Abstract
An effective synthetic approach for various 1,2,2-triarylethanones from triaryl substituted alkenes has been developed an electrochemical Wacker-type oxygenation with O as the sole oxygen source. It presents the first instance of the Wacker-type oxidation expanding its substrate scope to trisubstituted alkenes. The approach is transition-metal-free, compatible with various functional groups, and can be carried out under mild conditions resulting in satisfactory yields. Mechanistic experiments suggest the CO bond formation occurs through reactions between cationic carbon species and the superoxide radical, which involves the 1,2-shift of the electron-rich substituent.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d3cc05770d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Zeolite-Encaged Isolated Palladium Redox Centers toward Sustainable Wacker-Type Oxidations.
J Am Chem Soc
October 2024
Key Laboratory of Advanced Energy Materials Chemistry of Ministry of Education, College of Chemistry, Nankai University, Tianjin 300071, P. R. China.
The selective oxidation of olefins by molecular oxygen holds great importance in the chemical industry due to its remarkable adaptability in constructing carbonyl compounds. Classical homogeneous Wacker oxidation with a complex system of PdCl-CuCl-HO is currently employed in the industrial production of acetaldehyde, which suffers from several key drawbacks. The development of alternative heterogeneous catalytic systems for Wacker-type oxidations has been hotly pursued for decades.
View Article and Find Full Text PDFTotal Synthesis of the Bacterial -Quinol (+)-Strepantibin A through Iodyl-Type λ-Iodane-Promoted Asymmetric Hydroxylative Phenol Dearomatization.
Org Lett
July 2024
Université de Bordeaux, ISM (CNRS-UMR 5255), 351 cours de la Libération, 33405 Talence Cedex, France.
An enantioselective synthesis of the bacterial metabolite (+)-strepantibin A, a novel inhibitor of the hexokinase II (HK2) in cancer cells, is described. Its monomethylated resorcinolic -terphenyl core was conveniently prepared through a Danheiser benzannulation. The elaboration of its -quinolic chiral center was accomplished by relying on an iodyl-promoted regio- and enantioselective hydroxylative dearomatization.
View Article and Find Full Text PDFElectrochemical aerobic Wacker-type oxygenation of triaryl substituted alkenes to 1,2,2-triarylethanones.
Chem Commun (Camb)
March 2024
School of Chemical Engineering & Technology, China University of Mining and Technology, Xuzhou 221116, Jiangsu, P. R. China.
Article Synopsis
- * This is the first time Wacker-type oxidation has been applied to trisubstituted alkenes and the process does not require transition metals, making it versatile across different functional groups.
- * The reaction occurs under mild conditions and produces good yields, with the mechanism involving a C=O bond formation through interactions between carbon cations and superoxide radicals, aided by a 1,2-shift of an electron-rich substituent.
Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles.
RSC Adv
September 2023
Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University Xinxiang Henan 453007 China +86-373-332-5250.
A palladium(ii)-catalyzed intramolecular oxidative aza-Wacker-type reaction of vinyl cyclopropanecarboxamides to access a series of conformationally restricted highly substituted aza[3.1.0]bicycles is reported.
View Article and Find Full Text PDFOxidation of Organic Compounds Using Water as the Oxidant with H Liberation Catalyzed by Molecular Metal Complexes.
Acc Chem Res
August 2022
Department of Molecular Chemistry and Materials Science, The Weizmann Institute of Science, 234 Herzl Street, Rehovot 7610001, Israel.
Oxidation reactions of organic compounds play a central role in both industrial chemical and material synthesis as well as in fine chemical and pharmaceutical synthesis. While traditional laboratory-scale oxidative syntheses have relied on the use of strong oxidizers, modern large-scale oxidation processes preferentially utilize air or pure O as an oxidant, with other oxidants such as hydrogen peroxide, nitric acid, and aqueous chlorine solution also being used in some processes. The use of molecular oxygen or air as an oxidant has been very attractive in recent decades because of the abundance of air and the lack of wasteful byproduct generation.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!