P(MeNCH₂CH₂)₃N:  An Efficient Catalyst for the Desilylation of tert-Butyldimethylsilyl Ethers

Zhengkun Yu* and John G. Verkade

*Department of Chemistry, Iowa State University, Ames, Iowa 50011, Email: zkyudicp.ac.cn

Z. Yu, J. G. Verkade, J. Org. Chem., 2000, 65, 2065-2068.

DOI: 10.1021/jo991591i

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Abstract

tert-Butyldimethylsilyl (TBDMS) ethers of primary, secondary, and tertiary alcohols and phenolic TBDMS ethers are desilylated to their corresponding alcohols and phenols, respectively, in DMSO, at 80°C, in very good yield in the presence of P(MeNCH₂CH₂)₃N as catalyst. Desilylations of tert-butyldiphenylsilyl (TBDPS) ethers were much less effective.

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proposed mechanism

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Nonionic Superbase-Catalyzed Silylation of Alcohols

B. A. D'Sa, D. McLeod, J. G. Verkade, J. Org. Chem., 1997, 62, 5057-5061.

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Key Words

TBDMS Ethers, organocatalysis

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ID: J42-Y2000