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

作者:Bothwell Jason M; Angeles Veronica V; Carolan James P; Olson Margaret E; Mohan Ram S*
来源:Tetrahedron Letters, 2010, 51(7): 1056-1058.
DOI:10.1016/j.tetlet.2009.12.076

摘要

The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu(4)N(+)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.

  • 出版日期2010-2-17