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

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

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

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

Illinois Wesleyan University

Research output: Journal Article › Article › peer-review

Abstract

The most common method for the deprotection ofTBDMS 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 ofTBDMS, 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	American English
Journal	Tetrahedron Letters
Volume	51
State	Published - 2010

Disciplines

Organic Chemistry

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Cite this

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

year = "2010",

language = "American English",

volume = "51",

journal = "Tetrahedron Letters",

}

TY - JOUR

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

AU - Mohan, Ram S.

AU - Bothwell, Jason M.

AU - Angeles, Veronica V.

AU - Carolan, James P.

AU - Olson, Margaret E.

PY - 2010

Y1 - 2010

N2 - The most common method for the deprotection ofTBDMS 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 ofTBDMS, 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 ofTBDMS 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 ofTBDMS, 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.

M3 - Article

VL - 51

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -