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A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst
Tetrahedron Letters (2010)
  • Ram S. Mohan, Illinois Wesleyan University
  • Jason M. Bothwell
  • Veronica V. Angeles
  • James P. Carolan
  • Margaret E. Olson
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
Publication Date
2010
Publisher Statement
Tetrahedron Letters is published by Elsevier, www.elsevier.com/locate/tetlet. Article information: http://dx.doi.org/10.1016/j.tetlet.2009.12.076
Citation Information
Ram S. Mohan, Jason M. Bothwell, Veronica V. Angeles, James P. Carolan, et al.. "A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst" Tetrahedron Letters Vol. 51 Iss. 7 (2010)
Available at: http://works.bepress.com/ram_mohan/33/