Diiodine–Triethylsilane System: A Practical Method for Deprotection of Aryl Benzyl Ethers

Abstract A practical method for the debenzylation of aryl benzyl ethers has been developed using easy-to-operate I2 and Et3SiH, as well as the green solvent ethyl acetate. Halo, methoxy, ester, and nitro groups on the benzene ring of the aryl benzyl ether are compatible with this debenzylation. Control experiments revealed that Et3SiI, generated in situ, might be the actual promoter of the procedure. This method does not require a separate desilylation reaction to obtain phenol products.

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Publication Details

Journal
Synlett
Published
2024-09-13
DOI
https://doi.org/10.1055/a-2414-7887
Citations
3
Primary Topic
Chemical Synthesis and Reactions
Type
article
Field-Weighted Citation Impact
0.75

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article

Diiodine–Triethylsilane System: A Practical Method for Deprotection of Aryl Benzyl Ethers

Zhuo Wang, Jin Jiang
3 citations
Synlett
Chemical Synthesis and Reactions
0.75
article

Diiodine–Triethylsilane System: A Practical Method for Deprotection of Aryl Benzyl Ethers

Zhuo Wang, Jin Jiang
article en
3 citations

Abstract

Abstract A practical method for the debenzylation of aryl benzyl ethers has been developed using easy-to-operate I2 and Et3SiH, as well as the green solvent ethyl acetate. Halo, methoxy, ester, and nitro groups on the benzene ring of the aryl benzyl ether are compatible with this debenzylation. Control experiments revealed that Et3SiI, generated in situ, might be the actual promoter of the procedure. This method does not require a separate desilylation reaction to obtain phenol products.

SynlettVol. 36(07)
Green Chemistry (PL), Sichuan University of Science and Engineering (CN)
Natural Science Foundation of Sichuan Province
Clean water and sanitation
Openalex Percentile: Top 32%
Chemical Synthesis and Reactions
0.75
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