Continuous Flow Electrochemistry Enables Practical and Site‐Selective C−H Oxidation

Author:

Chen Tian‐Sheng1,Long Hao1,Gao Yuxing1,Xu Hai‐Chao12ORCID

Affiliation:

1. State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province College of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 China

2. Discipline of Intelligent Instrument and Equipment Xiamen University Xiamen 361005 China

Abstract

AbstractThe selective oxygenation of ubiquitous C(sp3)−H bonds remains a highly sought‐after method in both academia and the chemical industry for constructing functionalized organic molecules. However, it is extremely challenging to selectively oxidize a certain C(sp3)−H bond to afford alcohols due to the presence of multiple C(sp3)−H bonds with similar strength and steric environment in organic molecules, and the alcohol products being prone to further oxidation. Herein, we present a practical and cost‐efficient electrochemical method for the highly selective monooxygenation of benzylic C(sp3)−H bonds using continuous flow reactors. The electrochemical reactions produce trifluoroacetate esters that are resistant to further oxidation but undergo facile hydrolysis during aqueous workup to form benzylic alcohols. The method exhibits a broad scope and exceptional site selectivity and requires no catalysts or chemical oxidants. Furthermore, the electrochemical method demonstrates excellent scalability by producing 115 g of one of the alcohol products. The high site selectivity of the electrochemical method originates from its unique mechanism to cleave benzylic C(sp3)−H bonds through sequential electron/proton transfer, rather than the commonly employed hydrogen atom transfer (HAT).

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis

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