Cycloaddition reactions of azides and electron-deficient alkenes in deep eutectic solvents: pyrazolines, aziridines and other surprises
File(s)
Published version
Author(s)
Type
Journal Article
Abstract
The reaction of organic azides and electron‐deficient alkenes was investigated in a deep eutectic solvent. A series of highly substituted 2‐pyrazolines was successfully isolated and their formation rationalised by DFT calculations. The critical effect of substitution was also explored; even relatively small changes in the cycloaddition partners led to completely different reaction outcomes and triazolines, triazoles or enaminones can be formed as major products depending on the alkene employed.
Date Issued
2020-04-27
Date Acceptance
2020-03-10
Citation
Advanced Synthesis & Catalysis, 2020, 362 (9), pp.1877-1886
ISSN
1615-4150
Publisher
Wiley
Start Page
1877
End Page
1886
Journal / Book Title
Advanced Synthesis & Catalysis
Volume
362
Issue
9
Copyright Statement
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Identifier
https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201901614
Grant Number
EP/K030760/1
Subjects
Science & Technology
Physical Sciences
Chemistry, Applied
Chemistry, Organic
Chemistry
Alkenes
Azides
Cycloaddition
Heterocycles
Solvent Effects
1,3-DIPOLAR CYCLOADDITION
EFFICIENT CATALYST
CRYSTAL-STRUCTURE
ARYL AZIDES
CHEMISTRY
ACID
DELTA-2-1,2,3-TRIAZOLINES
HYDRAZINE
CUAAC
Organic Chemistry
0302 Inorganic Chemistry
0305 Organic Chemistry
0904 Chemical Engineering
Publication Status
Published online
Article Number
adsc.201901614
Date Publish Online
2020-03-10