Journal
ORGANIC LETTERS
Volume 23, Issue 2, Pages 514-518Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04026
Keywords
-
Categories
Funding
- Max-Planck Society
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under Germany's Excellence Strategy [EXC 2008/1, 390540038]
- Liebig Fellowship of the German Chemical Industry Fund (Fonds der Chemischen Industrie, FCI)
- Alexander von Humboldt Foundation
Ask authors/readers for more resources
A visible-light-mediated debenzylation method has been proposed to make benzyl ethers temporary protective groups, enabling new orthogonal protection strategies and compatibility with multiple functional groups simultaneously.
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available