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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
Scholarship:
Journal Article
Article
Peer-review

Open access

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.

Scholarship

Output type

Scholarship:
Journal Article
Article
Peer-review

Original language

American English

Journal (Volume, Issue Number)

Tetrahedron Letters (Volume 51)

Publication milestones

  • Published - 2010

Publication status

Published - 2010

Documents and links

Final published version, 2.1 MB
License:Unspecified