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tert-Buyldiphenylsilylethyl (“TBDPSE”):  A Practical Protecting Group for Phenols

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journal contribution
posted on 18.02.2005, 00:00 authored by Brian S. Gerstenberger, Joseph P. Konopelski
A new protection group for phenols, the 2-(tert-butyldiphenylsilyl)ethyl (TBDPSE) group, has been prepared and investigated. Protection of a variety of substituted phenols proceeds in good to excellent yield. The group is stable to mild acid, base, hydrogenolysis conditions, and lithium/halogen exchange on the protected phenol. Removal is achieved with strong acid or standard fluoride treatment.