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.