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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.guiryucd.ie

S. T. A. Shah, S. Singh, P. J. Guiry, J. Org. Chem., 2009, 74, 2179-2182.

DOI: 10.1021/jo802494t (free Supporting Information)


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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