Categories: C-N Bond Formation > Synthesis of azides >
Synthesis of aryl azides
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A copper(II)-catalyzed conversion of organoboron compounds into the
corresponding azide derivatives complements existing procedures for the
preparation of aryl azides and will greatly facilitate copper- and
ruthenium-catalyzed azide-alkyne cycloaddition reactions for the preparation of
diversely functionalized 1-aryl- or 1-heteroaryl-1,2,3-triazoles derivatives.
K. D. Grimes, A. Gupte, C. C. Aldrich, Synthesis, 2010,
1441-1448.
Aromatic azides are formed in high yield from arenediazonium tosylates and
sodium azide in water at room temperature. An in situ diazotization followed by
azidation in the presence of p-TsOH allows the direct transformation of
aromatic amines. Besides being experimentally simple, these methods do not
require any metal catalysis and provide clean products without purification.
K. V. Kutonova, M. E. Trusova, P. S. Postnikov, V. D. Filimonov, J. Parello, Synthesis, 2013, 45,
2706-2710.
Reaction of [ArN2][BF4] salts immobilized in [BMIM][PF6]
ionic liquid (IL) with TMSI and TMSN3 represents an efficient method
for the preparation of iodo- and azido-derivatives via dediazoniation. Using
TMSBr, competing fluorodediazoniation (ArF formation) and hydrodediazoniation (ArH
formation) were observed depending on the substituents on the benzenediazonium
cation.
A. Hubbard, T. Okazaki, K. K. Laali, J. Org. Chem., 2008,
73, 316-319.
Nine azidopyridines bearing a single fluorine, chlorine, or bromine atom were
prepared and examined by differential scanning calorimetry (DSC). The utility of
these versatile intermediates was demonstrated through their use in a variety of
Click reactions and the diversification of the halogen handles.
M. D. Mandler, A. P. Degnan, S. Zhang, D. Aulakh, K. Georges, B. Sandhu, A.
Sarjeant, Y. Zhu, S. C. Traeger, P. T. Cheng, B. A. Ellsworth, A. Regueiro-Ren, Org. Lett., 2022,
24,
799-803.