Categories: C-H Bond Formation >
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.