Related Experiment Video
Updated: Jun 16, 2025
Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds
Published on: September 27, 2024
A General Strategy for C(sp3)─H Bond Etherification via Quinoline Derivative-Mediated Electrolysis
Yousen Xu1, Hao Wu1, ChenXi Zhu1
1Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024, China.
None:
Electrooxidative coupling of C(sp3)─H bonds with nucleophiles offers an attractive method for constructing C─C and C─X bonds without sacrificial oxidants. However, the direct electrochemical approach requires the nucleophilic reagent to have a higher potential than the C(sp3)─H coupling partners, which restricts the substrate scope. In this study, a quinoline derivative is introduced as an electrochemical mediator, enabling efficient C─H bond etherification with reduced reliance on the electronic properties of substrates. The catalytic system demonstrates broad substrate compatibility, extending to C(sp3)─H coupling partners featuring a diverse range of C─H bonds, including tertiary benzylic C─H bonds and unactivated C(sp3)─H bonds. Mechanistic investigations confirm the role of the electrocatalyst in the hydrogen atom transfer (HAT) process. This method provides a versatile and efficient strategy for the late-stage functionalization of bioactive molecules.
Related Concept Videos
02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
03:00Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
02:45E2 Reaction: Kinetics and Mechanism
01:12Acid Halides to Esters: Alcoholysis
01:38Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
02:35Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...