One-Pot Hydroxy Group Activation/Carbon-Carbon Bond Forming Sequence Using a Bronsted Base/Bronsted Acid System

A new sequential two-step multicatalytic strategy is presented consisting in the efficient DBU-catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf2NH)-catalysed intermolecular alkylation by silicon-based nucleophiles and C-H nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1'-bi-2-naphthol (BINOL)-derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one-pot Bronsted base-Bronsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.