Copper-Catalyzed Electrophilic Amination of Organozinc Nucleophiles: Documentation of O-Benzoyl Hydroxylamines as Broadly Useful R₂N(+) and RHN(+) Synthons

Ashley M. Berman and Jeffrey S. Johnson*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, Email: jsjunc.edu

A. M. Berman, J. S. Johnson, J. Org. Chem., 2006, 71, 219-224.

DOI: 10.1021/jo051999h

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Abstract

A copper-catalyzed electrophilic amination of simple and functionalized aryl, heteroaryl-, benzyl, n-alkyl, sec-alkyl, and tert-alkyl diorganozinc nucleophiles with R₂NOC(O)Ph and RHNOC(O)Ph reagents as electrophilic nitrogen sources provides tertiary and secondary amines, respectively, in generally good yields. In many cases, the product may be isolated analytically pure after a simple extractive workup. A Cu-catalyzed amination of Grignard reagents using cocatalysis by ZnCl₂ is described.

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Key Words

Amines, Arylamines, Hydroxylamines

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ID: J48-Y2006-010