Categories: C-H Bond Formation >
Deaminations
Recent Literature
The use of an anomeric amide reagent enables a deamination of primary amines
and anilines under mild conditions and with remarkable functional group
tolerance including a range of pharmaceutical compounds, amino acids, amino
sugars, and natural products via formation of an isodiazene intermediate.
K. J. Berger, J. L. Driscoll, M. Yuan, B. D. Dherange, O. Gutierrez, M. D. Levin, J. Am. Chem. Soc.,
2021, 143, 17366-17373.
B(C6F5)3 catalyzes dehydrogenative couplings
of certain amines and hydrosilanes at elevated temperatures. At higher
temperature, the dehydrogenation pathway competes with cleavage of the C-N bond
and defunctionalization is obtained. This can be turned into a useful
methodology for the transition-metal-free reductive deamination of a broad range
of amines.
H. Fang, M. Oestreich, Angew. Chem. Int. Ed.,
2020, 59, 11394-11398.
Reductive deamination of aromatic amines can be conveniently carried out by
amination of the corresponding arylamine methanesulfonamides using chloroamine
under alkaline conditions. The intermediate aryl
methanesulfonylhydrazines eliminate methanesulfinic acid and nitrogen to afford
the desired deaminated products in high yield. The reaction tolerates a variety of
functional groups.
Y. Wang, F. S. Guziec, J. Org. Chem., 2001,
66, 8293-8296.