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

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), presum...

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Veröffentlicht in:Organometallics 2006-09, Vol.25 (20), p.4728-4730
Hauptverfasser: Ong, Tiow-Gan, O'Brien, Julie S, Korobkov, Ilia, Richeson, Darrin S
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0276-7333
1520-6041
DOI:10.1021/om060539r