期刊
ORGANIC LETTERS
卷 23, 期 2, 页码 514-518出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04026
关键词
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资金
- 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
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.
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