A K-Arylacetylide Complex for Catalytic Terminal Alkyne Functionalization using KOtBu as a Precatalyst

Herein we report a transition metal free catalytic terminal alkyne functionalization across the C-X triple bond (X = CH, N) with E-selective homo (alkyne-alkyne) and head-to-tail selective hetero (alkyne-nitrile) dimerization. A series of stoichiometric reactions enabled us to crystallize a reactive organometallic intermediate K-arylacetylide complex characterized by X-ray crystallography, indicating that an ionic mechanism is operative.