Categories: N-N Bond Formation >
Synthesis of Hydrazines (Hydrazides)
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Recent Literature
The electrophilic amination of primary aliphatic and aromatic amines with a
diethylketomalonate-derived oxaziridine affords the corresponding N-Boc
hydrazines in good to excellent yields. The method allows a one-pot synthesis of
pyrazoles from primary amines.
A. Armstrong, L. H. Jones, J. D. Knight, R. D. Kelsey, Org. Lett., 2005,
7, 713-716.
A small ring phosphacycle (phosphetane) catalyzes the synthesis of unsymmetrical
hydrazines by cross-selective intermolecular NN reductive coupling of
nitroarenes and anilines in the presence of a hydrosilane as the terminal
reductant. The reaction offers good chemoselectivity and functional group
tolerance.
G. Li, S. P. Miller, A. T. Radosevich, J. Am. Chem. Soc.,
2021, 143, 14464-14469.
A nickel-catalyzed N-N cross-coupling of O-benzoylated hydroxamates with
a broad range of aryl and aliphatic amines provides hydrazides in an up to 81%
yield. Experimental evidence implicates the intermediacy of electrophilic
Ni-stabilized acyl nitrenoids and the formation of a Ni(I) catalyst via
silane-mediated reduction.
J. P. Barbor, V. N. Nair, K. R. Sharp, T. D. Lohrey, S. E. Dibrell, T. K. Shah,
M. J. Walsh, S. E. Reisman, B. M. Stoltz, J. Am. Chem. Soc.,
2023, 145, 15071-15077.
A broadly applicable procedure for an aza-Lossen rearrangement converts
amines into complex hydrazine derivatives in two steps under safe, mild
conditions. This method allows the chemoselective formation of N-N bonds,
resulting in the synthesis of cyclic and acyclic products while avoiding side
reactions of the amphoteric (ambident) nitrogen-substituted isocyanate
intermediate.
D. E. Polat, D. D. Brzezinski, A. M. Beauchemin,
Org. Lett., 2019, 21, 4849-4852.