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A mild, efficient and selective deprotection of t-butyldimethylsilyl-protected phenols using cesium carbonate

โœ Scribed by Zhi-Yong Jiang; Yan-Guang Wang


Book ID
104253518
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
143 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


A mild and efficient method for the deprotection of aryl t-butyldimethysilyl (TBS) ethers is described. The protecting group TBS could be cleaved from aryl silyl ethers using cesium carbonate in DMF-H 2 O at room temperature to give the corresponding phenols in excellent yields. The reaction conditions allowed selective deprotection of aryl TBS-protected phenols in the presence of TBS, phenyloxycarbonyl or tetrahydropyranyl-protected alcohols.


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Selective deprotection of silyl-protecte
โœ R.David Crouch; Mike Stieff; Jessica L. Frie; Amy B. Cadwallader; Daniel C. Bevi ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 212 KB

Aryl silyl ethers can be deprotected to yield phenols in good to excellent yields using a biphasic system of 10 equivalents of NaOH and catalytic Bu4NHSO4 in 1,4dioxane. Alkyl silyl ethers prepared using a variety of silyl protecting groups survive under these conditions, allowing selective deprotec