Benzylation Reagents

The benzyl group has been widely used as a protective group of alcohols in organic synthesis, and various methods for benzylation have been reported. Benzyl halides are the most commonly used benzylation reagents and produce benzyl ethers in high yields under basic conditions.

In contrast, Benzyl 2,2,2-Trichloroacetimidate (1) is a benzylation reagent activated by acid-catalysts such as TfOH and used for the benzylation of base-sensitive substrates.^1a) 2 is more stable than 1, and reacts even with hindered alcohols in the presence of a catalytic amount of TMSOTf in dioxane to produce the benzylated products in high yields.^1b)