Categories: C-N Bond Formation > Amines >
Synthesis of hydroxylamines
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Recent Literature
With a simple two-step procedure involving substitution with readily available
TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared from
the corresponding alcohols, alkyl halides, or alkyl sulfonates without using
external oxidants.
K. Kitahara, T. Toma, J. Shimokawa, T. Fukuyama, Org. Lett., 2008,
10, 2259-2261.
The utilization of unprotected NH2OH, which is not only an oxygen nucleophile
but also a nitrogen nucleophile, in iridium-catalyzed allylic substitution
provides N-(1-allyl)hydroxylamines in good to high yields with high
level of chemoselectivities, regioselectivities, and enantioselectivities under mild,
carefully adjusted reaction conditions.
J. Chen, Q. Liang, X. Zhao,
Org. Lett., 2019, 21, 5383-5386.
Trimethoxyphenyliodonium(III) acetate serves as an efficient arylation
reagent for N,O-protected hydroxylamines, generating N-methoxysulfonylanilines
derivatives in the absence of transition metal catalysts. This amination
reaction is compatible with several protecting groups, including Troc, Cbz, Boc,
benzyl, acetyl, and silyl groups.
K. Kikushima, A. Morita, E. E. Elboray, T. Bae, N. Miyamoto, Y. Kita, T. Dohi, Synthesis, 2022, 54,
5191-5202.
The bis-pyrazole phosphine BippyPhos is an effective ligand for a smooth
palladium-catalyzed cross-coupling of hydroxylamines with aryl bromides,
chlorides, and iodides at 80°C in toluene in the presence of Cs2CO3
to give synthetically versatile N-arylhydroxylamine products in good to
excellent yield.
A. Porzelle, M. D. Woodrow, N. C. O. Tomkinson, Org. Lett., 2009,
11, 233-236.
An efficient method for the copper-catalyzed N-arylation of
hydroxylamines with aryl iodides allows the conversion of various N- and
O-functionalized hydroxylamines in good to excellent yield with a broad
range of aryl coupling partners. Methods for the selective deprotection of
either the N- or O-substituents for further functionalization are
also described.
K. L. Jones, A. Porzelle, A. Hall, M. D. Woodrow, N. C. O. Tomkinson, Org. Lett., 2008,
10, 797-800.
A highly regio- and enantioselective hydroxyamination of aldehydes with in situ
generated nitrosocarbonyl compounds from hydroxamic acid derivatives was
realized by combining TEMPO and BPO as oxidants in the presence of a
binaphthyl-modified amine catalyst.
T. Kano, F. Shirozu, K. Maruoka, J. Am. Chem. Soc., 2013,
135, 17735-17738.
Highly regioselective ring opening of epoxides with poor nucleophiles such as
indole, borane, O-trimethylsilylhydroxylamine, p-nitroaniline and
sterically hindered tert-butylamine is a fast and convenient reaction in
the presence of 5.0 M lithium perchlorate-Et2O solution (LPDE).
A. Heydari, M. Mehrdad, A. Maleki, N. Ahmadi, Synthesis, 2004,
1557-1558.