Access to α,α-dihaloacetophenones through anodic C C bond cleavage in enaminones

We have developed a method to synthesize alpha,alpha-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl-2 or Br-2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C=C of the N,N-dimethyl enam...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 88; pp. 153575 - 153581
Main Authors Zhang, Zhenlei, Yang, Jiusi, Wu, Kairui, Yu, Renjie, Bu, Jiping, Huang, Zijun, Li, Shaoke, Ma, Xiantao
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 05.01.2022
Subjects
ambient temperature
anodes
Chemistry
Chemistry, Organic
cleavage (chemistry)
electrochemistry
electrosynthesis
Physical Sciences
Science & Technology
SELECTIVE PREPARATION
alpha,alpha-Dihaloacetophenones
AMBIENT
EFFICIENT SYNTHESIS
ALPHA
ALKYNES
ELECTROCHEMICAL SYNTHESIS
KETONES
REDUCTION
Electrosynthesis
N,N-Dimethyl enaminone
Green chemistry
WATER
Online AccessGet full text

Cover

More Information
Summary:We have developed a method to synthesize alpha,alpha-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl-2 or Br-2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C=C of the N,N-dimethyl enaminone to generate alpha,alpha-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield. (C) 2021 Elsevier Ltd. All rights reserved.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.153575