Facile and Atom-Efficient Amidolithium-Catalyzed C−C and C−N Formation for the Construction of Substituted Guanidines and Propiolamidines

Lithium hexamethyldisilazide (LiN(SiMe3)2) is an excellent precatalyst for the room-temperature guanylation of a variety of aryl amines with carbodiimides and for the C−C coupling reaction between terminal alkynes and carbodiimides to yield propiolamidines. Tetramethylethylenediamine (TMEDA), presumably through modulation of the lithium coordination sphere, increases the reactivity of this catalyst system.