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.
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.
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.
