A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst

The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu 4N +F − (TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection of TBDMS, TES, and TIPS ethers using iron(III)...

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Bibliographic Details
Published in:Tetrahedron letters 2010-02, Vol.51 (7), p.1056-1058
Main Authors: Bothwell, Jason M., Angeles, Veronica V., Carolan, James P., Olson, Margaret E., Mohan, Ram S.
Format: Article
Language:English
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Summary:The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu 4N +F − (TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection of TBDMS, TES, and TIPS ethers using iron(III) tosylate as a catalyst. Phenolic TBDMS ethers, TBDPS ethers and the BOC group are not affected under these conditions. Iron(III) tosylate is an inexpensive, commercially available, and non-corrosive reagent.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.12.076