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

Jason M. Bothwell; Veronica V. Angeles; James P. Carolan; Margaret E. Olson; Ram S. Mohan

doi:10.1016/j.tetlet.2009.12.076

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

Jason M. Bothwell, Veronica V. Angeles, James P. Carolan, Margaret E. Olson, Ram S. Mohan

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu₄N⁺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.

Original language	English (US)
Pages (from-to)	1056-1058
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2009.12.076
State	Published - Feb 17 2010
Externally published	Yes

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10.1016/j.tetlet.2009.12.076

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

abstract = "The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+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.",

author = "Bothwell, {Jason M.} and Angeles, {Veronica V.} and Carolan, {James P.} and Olson, {Margaret E.} and Mohan, {Ram S.}",

year = "2010",

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T1 - A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst

AU - Bothwell, Jason M.

AU - Angeles, Veronica V.

AU - Carolan, James P.

AU - Olson, Margaret E.

AU - Mohan, Ram S.

PY - 2010/2/17

Y1 - 2010/2/17

N2 - The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+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.

AB - The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+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.

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DO - 10.1016/j.tetlet.2009.12.076

M3 - Article

AN - SCOPUS:73649140607

SN - 0040-4039

VL - 51

SP - 1056

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

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

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