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Synthesis of hydroxylamines and related compounds

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


A hypervalent iodine mediated reaction between carboxylic acids and N,N-dimethylformamide occurs under mild conditions at room temperature to provide O-aroyl-N,N-dimethylhydroxylamines in good yields, which are important electrophilic amination reagents. The process shows good functional group compatibility and air and moisture tolerance.
C. Zhang, Q. Yue, Z. Xiao, X. Wang, Q. Zhang, D. Li, Synthesis, 2017, 49, 4303-4308.