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

Authors

Ram Mohan, Illinois Wesleyan UniversityFollow
Jason Bothwell
Veronica Angeles
James Carolan
Margaret Olson

Publication Date

January 2010

Comments

Tetrahedron Letters is published by Elsevier, www.elsevier.com/locate/tetlet. Article information: http://dx.doi.org/10.1016/j.tetlet.2009.12.076

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.

Disciplines

Organic Chemistry

Recommended Citation

Mohan, Ram; Bothwell, Jason; Angeles, Veronica; Carolan, James; and Olson, Margaret, "A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst" (2010). Scholarship. 10.
https://digitalcommons.iwu.edu/chem_scholarship/10