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  5. Continuous Flow Synthesis of Cyclobutenes Using LED Technology
 
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Continuous Flow Synthesis of Cyclobutenes Using LED Technology

Author(s)
Smyth, Megan  
Moody, Thomas S.  
Wharry, Scott  
Baumann, Marcus  
Uri
http://hdl.handle.net/10197/24414
Date Issued
2023-05-04
Date Available
2023-05-10T10:08:34Z
Abstract
Cyclobutenes are highly strained ring systems of considerable synthetic interest that can be accessed via cycloaddition reactions between alkenes and alkynes. However, their traditional preparation relies on photochemical [2+2]-cycloadditions that exploit low wavelength UV radiation emitted from inefficient medium-pressure Hg-lamps. This paper reports on the development of a modern approach using a high-power LED set-up emitting at the boundary of UV-A and visible light in conjunction with a continuous flow reactor. The resulting flow process renders a series of cyclobutenes from maleimides and various commercial alkynes. This provides a more energy-efficient approach that is readily scalable to access multigram quantities of cyclobutenes in high chemical yields and short residence times. The value of these products is exemplified by flow-based hydrogenations yielding highly substituted cyclobutanes which represent sought after building blocks in modern medicinal chemistry programs.
Sponsorship
Science Foundation Ireland
Other Sponsorship
Frontiers for the Future
Type of Material
Journal Article
Publisher
Georg Thieme Verlag
Journal
Accounts and Rapid Communications in Chemical Synthesis (Synlett)
Volume
24
Issue
35
Start Page
285
End Page
290
Copyright (Published Version)
2023 Thieme
Subjects

Photochemistry

Cycloaddition

Cyclobutene

Light emitting diode ...

Flow chemistry

DOI
10.1055/a-2086-0630
Language
English
Status of Item
Peer reviewed
ISSN
0936-5214
This item is made available under a Creative Commons License
https://creativecommons.org/licenses/by/3.0/ie/
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AAM_manuscript.pdf

Size

566.67 KB

Format

Adobe PDF

Checksum (MD5)

3c8b407f7637145f6c8d85d212a2b7ce

Owning collection
Chemistry Research Collection

Item descriptive metadata is released under a CC-0 (public domain) license: https://creativecommons.org/public-domain/cc0/.
All other content is subject to copyright.

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