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N-Iodosuccinimide (NIS) as a mild and highly chemoselective catalyst for deprotection of tert-butyldimethylsilyl ethers

Babak Karimi, Asghar Zamani and Daryoush Zareyee

*Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), PO Box 45195-159, Gava Zang, Zanjan, Iran, Email: karimiiasbs.ac.ir

B. Karimi, A. Zamani, D. Zarayee, Tetrahedron Lett., 2004, 45, 9139-9141.

DOI: 10.1016/j.tetlet.2004.09.157


Abstract

Various tert-butyldimethylsilyl ethers are easily removed in excellent yields by treatment with a catalytic amount of N-iodosuccinimide in methanol. This method allows a selective deprotection of TBDMS ethers of alcohols in the presence of TBDMS ethers of phenols.

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Details

The document discusses a study on the use of N-Iodosuccinimide (NIS) as a mild and highly chemoselective catalyst for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers. The research, conducted by Babak Karimi, Asghar Zamani, and Daryoush Zareyee, demonstrates that a catalytic amount of NIS (5 mol%) in methanol can effectively remove TBDMS groups from a variety of alcoholic ethers, yielding the corresponding alcohols in good to excellent yields. This method is particularly notable for its ability to selectively deprotect alcoholic TBDMS ethers in the presence of phenolic TBDMS ethers, which remain stable under the reaction conditions. The procedure involves stirring the TBDMS ether with NIS in methanol at room temperature, followed by isolation of the product through filtration and solvent evaporation. The study highlights the advantages of this method, including mild reaction conditions, high selectivity, and the use of inexpensive reagents. The results are summarized in a table showing the deprotection of various substrates, with yields ranging from 69% to 100%. This method offers a valuable alternative to existing deprotection techniques, which often involve harsh conditions or expensive reagents.


Key Words

Silyl ethers, Deprotection, N-Iodosuccinimide, TBDMS ethers, Protecting groups


ID: J72-Y2004-2430