Paired electrochemical C-H bromination of (hetero)arenes with 2-bromoethan-1-ol

A site-selective electrochemical C-H bromination of (hetero)arenes with 2-bromoethan-1-ol through paired electrolysis has been developed. The C-H bromination reactions depend on the anodic oxidation of Br- produced by the cathodic reduction of 2-bromoethan-1-ol with available ethylene oxide and hydr...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 4; pp. 990 - 995
Main Authors Lv, Yanxia, Hou, Zhong-Wei, Li, Pinhua, Wang, Lei
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.02.2023
Royal Society of Chemistry
Subjects
Anodizing
Aromatic compounds
Bromination
Chemical reduction
Chemistry
Chemistry, Organic
Electrochemistry
Electrolysis
Ethylene oxide
Functional groups
Hydrogen evolution
Organic chemistry
Oxidation
Physical Sciences
Room temperature
Science & Technology
MEDICINAL CHEMISTRY
HALIDE
ARENES
COORDINATION
HALOGENATION
AROMATIC-COMPOUNDS
EFFICIENT
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Summary:A site-selective electrochemical C-H bromination of (hetero)arenes with 2-bromoethan-1-ol through paired electrolysis has been developed. The C-H bromination reactions depend on the anodic oxidation of Br- produced by the cathodic reduction of 2-bromoethan-1-ol with available ethylene oxide and hydrogen evolution. The method has good compatibility with common functional groups and the scale-up electrolysis can easily be performed. A wide variety of brominated products were obtained with satisfactory yields at room temperature in a simple undivided cell.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d2qo01425d