A Novel, Chemoselective and Efficient Microwave-Assisted Deprotection of Silyl Ethers with Selectfluor
Syed Tasadaque A. Shah, Surendra Singh and Patrick J. Guiry*
*Centre for Synthesis and Chemical Biology, School of
Chemistry and Chemical Biology, UCD Conway Institute, University College Dublin,
Belfield, Dublin 4, Ireland, Email: p.guiry
ucd.ie
S. T. A. Shah, S. Singh, P. J. Guiry, J. Org. Chem., 2009, 74, 2179-2182.
DOI: 10.1021/jo802494t
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Abstract
A microwave-assisted, chemoselective and efficient method for the cleavage of silyl ethers is catalyzed by Selectfluor. A wide range of TBDMS-, TIPS-, and TBDPS-protected alkyl silyl ethers can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. In addition, the transetherification and etherification of benzylic hydroxy groups in alcoholic solvents is observed.
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Key Words
TBDMS ethers, TBDPS ethers, etherification, microwave synthesis
ID: J42-Y2009-0760
