<div class="csl-bib-body">
<div class="csl-entry">Ehrschwendtner, F., Pálvölgyi, Á. M., Schröder, K., & Schnürch, M. (2024, July 9). <i>Catalyst-Free Visible Light-Driven Hydroacylation by Direct Photoexcitation of 4-Acyl Hantzsch Esters</i> [Poster Presentation]. 9th EuChemS Chemistry Congress, Dublin, Ireland. http://hdl.handle.net/20.500.12708/206115</div>
</div>
-
dc.identifier.uri
http://hdl.handle.net/20.500.12708/206115
-
dc.description.abstract
Hydroacylation is a powerful technique, that allows the formation of carbon-carbon bonds already functionalised by a ketone group and therefore synthetically useful. As it has been shown by Zhu et al. and Akiyama et al. benzothiazolines 2 have been used as hydroacylation reagents on electron-poor substrates 1. In both cases, aromatisation to benzothiazole (5) expels an acyl radical as soon as a radical is generated on benzothiazolines nitrogen. While Zhu et al. achieved this by creating a photolabile N-I-bond using hydroxybenziodoxolone (3) as an additive, Akiyama et al. used Ru(bpy)3Cl2.6H2O as photosensitiser. In both cases, however, additives or catalysts are needed. Additionally, Melchiorre et al. showed in a control reaction, that Hantzsch esters can act as a reservoir for alkyl radicals. Herein4, we present an alternative photochemical hydroacylation strategy for electron-poor alkenes 6 by the adaptation of Hantzsch esters 7 as a reservoir for acyl radicals, which can then be released upon direct photoexcitation without the need for any catalyst or additive. Furthermore, benzylidenemalononitrile-derived products 8 turned out to be easily oxidized to their fully conjugated counterpart by the addition of DDQ.
(figure cannot be displayed)
Figure 1. General idea and overview.
References
[1] Zhu et al., Org. Lett., 2019, 21, 5462-5466.
[2] Akiyama et al., Chem. Commun., 2019, 55, 11171-11174.
[3] Melchiorre et al., Angew. Chem. Int. Ed., 2017, 56, 15039-15043.
[4] Bica-Schröder et al., Org. Biomol. Chem., 2022, 20, 7245-7249.
en
dc.description.sponsorship
European Commission
-
dc.language.iso
en
-
dc.subject
catalyst-free
en
dc.subject
visible light
en
dc.subject
hydroacylation
en
dc.title
Catalyst-Free Visible Light-Driven Hydroacylation by Direct Photoexcitation of 4-Acyl Hantzsch Esters
en
dc.type
Presentation
en
dc.type
Vortrag
de
dc.contributor.affiliation
TU Wien, Austria
-
dc.relation.grantno
7465546 - 04/12/2019
-
dc.type.category
Poster Presentation
-
tuw.project.title
Kontinourliche Umsetzung von CO2 in ionischen Flüssigkeiten
-
tuw.researchTopic.id
X1
-
tuw.researchTopic.name
Beyond TUW-research focus
-
tuw.researchTopic.value
100
-
tuw.publication.orgunit
E163 - Institut für Angewandte Synthesechemie
-
tuw.author.orcid
0000-0001-8138-0831
-
tuw.author.orcid
0000-0002-2515-9873
-
tuw.author.orcid
0000-0003-2946-9294
-
tuw.event.name
9th EuChemS Chemistry Congress
-
tuw.event.startdate
07-07-2024
-
tuw.event.enddate
11-07-2024
-
tuw.event.online
On Site
-
tuw.event.type
Event for scientific audience
-
tuw.event.place
Dublin
-
tuw.event.country
IE
-
tuw.event.presenter
Ehrschwendtner, Florian
-
wb.sciencebranch
Chemie
-
wb.sciencebranch.oefos
1040
-
wb.sciencebranch.value
100
-
item.cerifentitytype
Publications
-
item.languageiso639-1
en
-
item.fulltext
no Fulltext
-
item.openairetype
conference poster not in proceedings
-
item.openairecristype
http://purl.org/coar/resource_type/c_18co
-
item.grantfulltext
none
-
crisitem.project.funder
European Commission
-
crisitem.project.grantno
7465546 - 04/12/2019
-
crisitem.author.dept
E163-03-5 - Forschungsgruppe Nachhaltige organische Synthese und Katalyse
-
crisitem.author.dept
E163-03-5 - Forschungsgruppe Nachhaltige organische Synthese und Katalyse
-
crisitem.author.dept
E163-03-5 - Forschungsgruppe Nachhaltige organische Synthese und Katalyse
-
crisitem.author.dept
E163 - Institut für Angewandte Synthesechemie
-
crisitem.author.orcid
0000-0002-2515-9873
-
crisitem.author.orcid
0000-0003-2946-9294
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
