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  4. Formal Aza-Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis
 
research article

Formal Aza-Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis

Yi, Xiangli  
•
Hu, Xile  
March 26, 2019
Angewandte Chemie International Edition

In oxidative electrochemical organic synthesis, radical intermediates are often oxidized to cations on the way to final product formation. Herein, we describe an approach to transform electrochemically generated organic radical intermediates into neutral products by reaction with a metal catalyst. This approach combines electrochemical oxidation with Cu catalysis to effect formal aza-Wacker cyclization of internal alkenes. The Cu catalyst is essential for transforming secondary and primary alkyl radical intermediates into alkenes. A wide range of 5-membered N-heterocycles including oxazolidinone, imidazolidinone, thiazolidinone, pyrrolidinone, and isoindolinone can be prepared under mild conditions.

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Type
research article
DOI
10.1002/anie.201814509
Web of Science ID

WOS:000462622700044

Author(s)
Yi, Xiangli  
Hu, Xile  
Date Issued

2019-03-26

Publisher

Wiley-VCH Verlag GmbH

Published in
Angewandte Chemie International Edition
Volume

58

Issue

14

Start page

4700

End page

4704

Subjects

Chemistry, Multidisciplinary

•

Chemistry

•

alkene functionalization

•

aza-wacker cyclization

•

copper

•

electrochemical organic synthesis

•

radical reactions

•

amination

•

functionalization

•

radicals

•

alkenes

•

olefins

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSCI  
Available on Infoscience
June 18, 2019
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/156973
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