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.