The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide

An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the pre...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2008-01, Vol.6 (12), p.2168-2172
Main Authors: Shah, Syed Tasadaque A, Guiry, Patrick J
Format: Article
Language:English
Subjects:
Ethers
Magnetic Resonance Spectroscopy
Trimethylsilyl Compounds - chemistry
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Summary:An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The deprotection of silyl esters was also achieved employing catalytic quantities of TMSBr.
ISSN:1477-0520
1477-0539
DOI:10.1039/b803949f