N-Functionalized organolithium compounds via tellurium/lithium exchange reaction

A set of tellurium amines have been evaluated in the tellurium/lithium exchange reaction. The nitrogen-containing organolithium compounds were efficiently prepared by using N-Bz tellurium amines and a mixture of n-butyllithium and lithium naphthalenide (LiNp) for performing the exchange reaction. The corresponding dianion intermediates were trapped with a wide range of electrophiles, furnishing the corresponding products in good to excellent yields. The reaction was also employed in the synthesis of phenethylamines.