dc.contributor.author
Cavedon, Cristian
dc.contributor.author
Sletten, Eric T.
dc.contributor.author
Madani, Amiera
dc.contributor.author
Niemeyer, Olaf
dc.contributor.author
Seeberger, Peter H.
dc.contributor.author
Pieber, Bartholomaeus
dc.date.accessioned
2021-08-09T13:26:28Z
dc.date.available
2021-08-09T13:26:28Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/31574
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-31306
dc.description.abstract
The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.
en
dc.format.extent
5 Seiten
dc.rights.uri
https://creativecommons.org/licenses/by/4.0/
dc.subject
Protective groups
en
dc.subject
Pharmaceuticals
en
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
dc.title
Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
dc.type
Wissenschaftlicher Artikel
dcterms.bibliographicCitation.doi
10.1021/acs.orglett.0c04026
dcterms.bibliographicCitation.journaltitle
Organic Letters
dcterms.bibliographicCitation.number
2
dcterms.bibliographicCitation.pagestart
514
dcterms.bibliographicCitation.pageend
518
dcterms.bibliographicCitation.volume
23
dcterms.bibliographicCitation.url
https://doi.org/10.1021/acs.orglett.0c04026
refubium.affiliation
Biologie, Chemie, Pharmazie
refubium.affiliation.other
Institut für Chemie und Biochemie
refubium.resourceType.isindependentpub
no
dcterms.accessRights.openaire
open access
dcterms.isPartOf.eissn
1523-7052
refubium.resourceType.provider
WoS-Alert