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

29 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

Publisher link

10.1016/j.tetlet.2009.12.076

Find It

Find It at U of M Libraries

Cite this

@article{26e73551ff7540b28bdf57a38197bc4f,

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",

month = feb,

day = "17",

doi = "10.1016/j.tetlet.2009.12.076",

language = "English (US)",

volume = "51",

pages = "1056--1058",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "7",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/73649140607

UR - https://www.scopus.com/pages/publications/73649140607#tab=citedBy

U2 - 10.1016/j.tetlet.2009.12.076

DO - 10.1016/j.tetlet.2009.12.076

M3 - Article

AN - SCOPUS:73649140607

SN - 0040-4039

VL - 51

SP - 1056

EP - 1058

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

Abstract

Publisher link

Find It

Other files and links

Fingerprint

Cite this