zinc bromide

Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes

Zinc(II) bromide catalyzes the addition of terminal acetylenes to both saturated and unsaturated aldehydes in good to excellent yield at room temperature in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and Hunig's base (i-Pr2NEt). No reaction is observed under similar conditions in the absence of TMSOTf. Desilylation of the initial product provides access to synthetically useful propargyllic alcohols.