Electrophilic amination of organozinc halides

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...

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Bibliographic Details
Published in:Tetrahedron letters 1998-12, Vol.39 (50), p.9157-9160
Main Authors: Velarde-Ortiz, Raffet, Guijarro, Albert, Rieke, Reuben D.
Format: Article
Language:English
Subjects:
Amination
Azo compounds
Hydrazides
Zinc and compounds
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Summary: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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02108-X