Categories: N-O Bond Formation >
Synthesis of hydroxylamines and related compounds
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Recent Literature
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 0°C
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.