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 (free Supporting Information)
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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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B. A. D'Sa, D. McLeod, J. G. Verkade, J. Org. Chem., 1997, 62, 5057-5061.