Raffet Velarde-Ortiz, A. Guijarro, R. Rieke
Dec 10, 1998
Citations
0
Influential Citations
29
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The reaction of several functionalized primary, secondary and tertiary organozinc bromides, benzylzinc bromide, functionalized arylzinc halides and one heteroarylzinc bromide with di tert -butyl azodicarboxylate is described. The reaction products, N,N′ -di tert -butoxycarbonylhydrazino derivatives are obtained in excellent yields for most aliphatic substrates and good yields for aromatic substrates. These compounds are direct precursors of hydrazino and amino derivatives by deprotection. The process constitutes the first synthetically useful electrophilic amination of organozinc derivatives, and takes advantage of the broad functional group tolerance of the organozinc chemistry.