A mild, efficient and selective deprotection of t-butyldimethylsilyl-protected phenols using cesium carbonate
โ 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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โฆ 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.
๐ SIMILAR VOLUMES
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