DMF-mediated deprotection of bulky silyl esters under neutral and fluoride-free conditions

[Display omitted] Bulky TBDPS and TIPS carboxylic esters were efficiently cleaved by a green and mild protocol using only DMF–H2O (20:1) at 70°C. The neutral conditions tolerate various common acid- and base-labile functionalities, including alkyl and aryl silyl ethers.

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Bibliographic Details
Published in:Tetrahedron letters 2016-01, Vol.57 (3), p.253-255
Main Authors: Chen, Bo, Sun, Hui-Xia, Qin, Jian-Feng, Wang, Bing
Format: Article
Language:English
Subjects:
Green chemistry
Lewis base
Protective groups
Synthetic methods
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Description
Summary:[Display omitted] Bulky TBDPS and TIPS carboxylic esters were efficiently cleaved by a green and mild protocol using only DMF–H2O (20:1) at 70°C. The neutral conditions tolerate various common acid- and base-labile functionalities, including alkyl and aryl silyl ethers.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.11.048