Lithium hexamethyldisilazide (LiN(SiMe 3 ) 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.
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Ong et al. (2006) studied this question.
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