Oxidative Intramolecular Coupling of Amidocuprates as a Novel Route to Amines and Hydrazines.
Amidocuprates, derived from organocopper reagents and lithium amides upon exposure to oxygen at low temperature, provide new amine derivatives in satisfactory yields. Details of this flexible and simple methodology are given. The reaction mechanism is analyzed in terms of an oxidative intramolecular coupling of aminyl radicals with the ligands on Cu in the intermediate amidocuprate. This reaction is a mild and efficient method for N-alkylation, -vinylation, and -arylation by which a number of amines, not easily accessible by normal routes, can be synthesized. Once applied to lithium hydrazides, it also provides a new and straightforward entry to N-substituted hydrazines.
Alberti
Angelo
A
Dipartimento di Chimica Organica "A. Mangini", Facoltà di Chimica Industriale, Via Risorgimento 4, I-40136 Bologna, Italy, and Istituto dei Composti del Carbonio Contenenti Eteroatomi del CNR, Area di Ricerca di Bologna, Via P. Gobetti 101, I-40129 Bologna, Italy.
Canè
Francesco
F
Dembech
Pasquale
P
Lazzari
Dario
D
Ricci
Alfredo
A
Seconi
Giancarlo
G