Electrophilic amination of organozinc halides

✍ Scribed by Raffet Velarde-Ortiz; Albert Guijarro; Reuben D. Rieke

• Book ID: 104260269
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 206 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02108-x

✦ Synopsis

The reaction of several functionalized primary, secondary and tertiary organozinc bromides, benzylzinc bromide, functionalized arylzine halides and one heteroarylzine bromide with ditert-butyl azodicarboxylate is described. The reaction products, N,N'-ditert-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 eleetrophilic amination of organozinc derivatives, and takes advantage of the broad functional group tolerance of the organozinc chemistry.