An Efficient Protocol for Selective Silylation of Hydroxy Group Using N,O-Bis(tert-butyldimethylsilyl)acetamide and N,N-Dimethyl-4-aminopyridine N-Oxide br

An efficient method for the silylation of alcohols was developed using N,O-bis(tert-butyldimethylsilyl)acetamide oxide (DMAPO). Monosilylation of 1,2-diols was successfully experiments revealed that a phenolic hydroxy group was silylated much faster than a primary alcohol in both an inter- and intramolecular manner. The reactivity toward silylation under these systems might stem from the pKa of the hydroxy group.

Automated summary

An efficient method for silylation of alcohols using DMAPO as a reagent has been developed. Experimental results showed that the silylation of phenolic hydroxy group was much faster than that of primary alcohols, which might be attributed to the acidity (pKa value) of the hydroxy group.