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Synthesis of hydroxylamines and related compounds

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Choline peroxydisulfate - an oxidizing task-specific ionic liquid - enables the preparation of N,N-disubstituted hydroxylamines from secondary amines. This method offers operational simplicity, high selectivity, and green reaction conditions.
A. Banan, H. Valizadeh, A. Heydari, A. Moghimi, Synlett, 2017, 28, 2315-2319.


Magnesium dialkylamides react with alcohol-derived 2-methyl-2-tetrahydropyranyl alkyl peroxides (MTHPs) in tetrahydrofuran at 0C to give N,N,O-trisubstituted hydroxylamines in very good yields. A wide range of substrates are compatible with the described reaction.
J. Hill, A. A. Hettikankanamalage, D. Crich, J. Am. Chem. Soc., 2020, 142, 14286-14294.


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.


The reaction of magnesium amides with tert-butyl 2,6-dimethyl perbenzoate in tetrahydrofuran at 0 C provides O-tert-Butyl-N,N-disubstituted hydroxylamines by direct N-O bond formation with a broad functional group tolerance. A reaction mechanism is presented to account for the observed reactivity.
J. Hill, D. Crich, Org. Lett., 2021, 23, 6337-6341.


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.