Hydrazine
See also: methylhydrazine, p-toluenesulfonyl hydrazide
Name Reactions
Recent Literature
Various olefins can be hydrogenated quantitatively with neutral,
flavin-derived catalysts in the presence of hydrazine under an
athomspheric pressure of O2. A vitamin B2 derivative acts
as a highly efficient and robust catalyst for the environmentally benign
process producing water and nitrogen gas as the only waste products.
Y. Imada, T. Kitagawa, T. Ohno, H. Iida, T. Naota, Org. Lett., 2010,
12, 32-35.
Olefins can be hydrogenated by treatment with hydrazine in the presence
of a 5-ethyl-3-methyllumiflavinium perchlorate catalyst under O2
atmosphere to give the corresponding hydrogenated products in excellent
yields along with environmentally benign water and molecular nitrogen as
the only waste products.
Y. Imada, H. Iida, T. Naota, J. Am. Chem. Soc., 2005, 127, 14544-14545.
Whereas an Ir-catalyzed alcohol deoxygenation on basis of dehydrogenation/Wolff-Kishner
reduction is efficient mainly with activated alcohols under harsh reaction
conditions, a Ru-catalyzed aliphatic primary alcohol deoxygenation offers good
functional group tolerance and excellent efficiency under practical reaction
conditions. Its synthetic utility is further illustrated by complete chemo- and
regio-selectivity in complex molecular settings.
X.-J. Dai, C.-J. Li, J. Am. Chem. Soc., 2016,
138, 5344-5440.
V2O5/TiO2 as a heterogeneous and recyclable
catalyst mediates a hydrogenation of nitro compounds to their corresponding
amines under irradiation of blue LEDs at ambient temperature. Hydrazine hydrate
is used as a reductant and ethanol is used as a solvent, facilitating green,
sustainable, low-cost production.
S. Kumar, S. K. Maurya, J. Org. Chem., 2023, 88,
8690-8702.
Several bromo, chloro, iodo and multihalogenated nitroarenes have been
selectively reduced with hydrazine hydrate in the presence of Pd/C to give the
corresponding halogenated anilines in good yield. Using microwave irradiation at
elevated temperature and pressure, dehalogenated products can be isolated.
F. Li, B. Frett, H.-y Li,
Synlett, 2014, 25, 1403-1408.
Visible-light mediates a scalable and operationally simple method for the
chemoselective deoxygenation of a wide range of N-heterocyclic N-oxides
at room temperature using only commercially available reagents. This protocol
offers an unprecedented chemoselective removal of the oxygen atom in a quinoline
N-oxide in the presence of a pyridine N-oxide through the
judicious selection of the photocatalyst.
K. D. Kim, J. H. Lee, Org. Lett.,
2018, 20, 7712-7716.
The use of hydrazine under basic conditions enables an efficient and general
construction of quinoline N-oxides from ortho-nitro chalcones via
umpolung of carbonyl groups. This transition-metal free method offers good functional group tolerance, environmental
friendliness, and mild reaction conditions with nitrogen gas as byproduct.
G. Zhang, K. Yang, S. Wang, Q. Feng, Q. Song, Org. Lett., 2021, 23,
595-600.
Related
A selective photoinduced reduction of nitroarenes to N-arylhydroxylamines
proceeds with a broad scope, excellent functional-group tolerance, and high
yields in the absence of catalyst or additives and uses only light and
methylhydrazine.
M. G. Kallitsaki, D. I. Ioannou, M. A. Terzidis, G. E. Kostakis, J. N.
Lykakis,
Org. Lett., 2020, 22, 4339-4343.
A facile protocol for the reduction of aromatic ketones and aldehydes to the
corresponding methylene unit involves the synthesis of a carbomethoxyhydrazone
intermediate that is easily decomposed to the reduced product. The reaction
avoids the use of pernicious hydrazine.
P. B. Cranwell, A. T. Russell, C. D. Smith,
Synlett, 2016, 27, 131-135.