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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 (free Supporting Information)


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


ID: J48-Y2006-010