Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

[Image: see text] 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, enabl...

Descripción completa

Detalles Bibliográficos
Autores principales: Cavedon, Cristian, Sletten, Eric T., Madani, Amiera, Niemeyer, Olaf, Seeberger, Peter H., Pieber, Bartholomäus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7880570/
https://www.ncbi.nlm.nih.gov/pubmed/33400534
http://dx.doi.org/10.1021/acs.orglett.0c04026
_version_ 1783650725790744576
author Cavedon, Cristian
Sletten, Eric T.
Madani, Amiera
Niemeyer, Olaf
Seeberger, Peter H.
Pieber, Bartholomäus
author_facet Cavedon, Cristian
Sletten, Eric T.
Madani, Amiera
Niemeyer, Olaf
Seeberger, Peter H.
Pieber, Bartholomäus
author_sort Cavedon, Cristian
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-7880570
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-78805702021-02-16 Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups Cavedon, Cristian Sletten, Eric T. Madani, Amiera Niemeyer, Olaf Seeberger, Peter H. Pieber, Bartholomäus Org Lett [Image: see text] 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. American Chemical Society 2021-01-05 2021-01-15 /pmc/articles/PMC7880570/ /pubmed/33400534 http://dx.doi.org/10.1021/acs.orglett.0c04026 Text en © 2021 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Cavedon, Cristian
Sletten, Eric T.
Madani, Amiera
Niemeyer, Olaf
Seeberger, Peter H.
Pieber, Bartholomäus
Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
title Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
title_full Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
title_fullStr Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
title_full_unstemmed Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
title_short Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
title_sort visible-light-mediated oxidative debenzylation enables the use of benzyl ethers as temporary protecting groups
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7880570/
https://www.ncbi.nlm.nih.gov/pubmed/33400534
http://dx.doi.org/10.1021/acs.orglett.0c04026
work_keys_str_mv AT cavedoncristian visiblelightmediatedoxidativedebenzylationenablestheuseofbenzylethersastemporaryprotectinggroups
AT slettenerict visiblelightmediatedoxidativedebenzylationenablestheuseofbenzylethersastemporaryprotectinggroups
AT madaniamiera visiblelightmediatedoxidativedebenzylationenablestheuseofbenzylethersastemporaryprotectinggroups
AT niemeyerolaf visiblelightmediatedoxidativedebenzylationenablestheuseofbenzylethersastemporaryprotectinggroups
AT seebergerpeterh visiblelightmediatedoxidativedebenzylationenablestheuseofbenzylethersastemporaryprotectinggroups
AT pieberbartholomaus visiblelightmediatedoxidativedebenzylationenablestheuseofbenzylethersastemporaryprotectinggroups

Ejemplares similares