Copper catalysed alkynylation of tertiary amines with CaC2 via sp(3) C-H activation

A mild and easy-to-handle protocol to produce propargylamines with a terminal alkyne through catalytic cross-coupling of tertiary amines and calcium carbide has been developed. The reaction proceeds via sp(3) C-H bond activation and C-C coupling. Good to excellent yields were obtained for the corresponding propargylamines with both alkyl and aryl substitutions. The development of these functionalized propargylamines with a terminal alkyne group will offer a wider application for the synthesis of natural or pharmaceutical products due to their unique sp C-H reactivity.