ArticleOrganic letters2021
Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups.
Article in Organic letters, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 66 citations in OpenAlex.
- Total Synthesis of Benthol A: Evidence for a Structure Revision.Journal of the American Chemical Society · 2026Article
- Deprotection of benzyl ethersGreen chemistry : an international journal and green chemistry resource : GC · 2026Article
- Sustainable Approaches for the Protection and Deprotection of Functional Groups.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Polarity-Driven Thiyl Radical-Catalyzed Aerobic Debenzylation of Ethers and Amines.The Journal of organic chemistry · 2024Article
- Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry.Chemical science · 2024Review
- Mechanistic investigations of polyaza[7]helicene in photoredox and energy transfer catalysis.Beilstein journal of organic chemistry · 2024Article
- Visible Light Photoredox-Catalyzed Decarboxylative Alkylation of 3-Aryl-Oxetanes and Azetidines via Benzylic Tertiary Radicals and Implications of Benzylic Radical Stability.The Journal of organic chemistry · 2023Article
- SnClMolecules (Basel, Switzerland) · 2022Article
- Alternatives to Iridium: A Polyaza[7]helicene as a Strongly Reductive Visible Light Photoredox Catalyst.ACS organic & inorganic Au · 2022Article
- A unified strategy for the total syntheses of eribulin and a macrolactam analogue of halichondrin B.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.Chemical reviews · 2022Review
- DDQ as a versatile and easily recyclable oxidant: a systematic review.RSC advances · 2021Review
- Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Article
- Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways*.Angewandte Chemie (International ed. in English) · 2021Article
- Emerging concepts in photocatalytic organic synthesis.iScience · 2021Review
- Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups.Organic letters · 2021Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
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.
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Registered trials
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