Copper/Diethyl Azodicarboxylate Mediated Regioselective Alkynylation of Unactivated Aliphatic Tertiary Methylamine with Terminal Alkyne

Mediated by copper/diethyl azodicarboxylate, regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne was successfully established. It is not necessary for the tertiary methylamines to be aryl substituted to modulate the properties of amines. The alkynylation reaction described here has the advantage of simple operation, mild reaction conditions, good to excellent yields, and no need to exclude air and moisture.