Cleavage of C-N bonds

Recent Literature

Optically pure C₂-symmetrical cyclic amines were efficiently synthesized from the corresponding diols obtained from an enantioselective borohydride reduction of diketones in the presence of a chiral β-ketoiminato cobalt(II) catalyst.
M. Sato, Y. Gunji, T. Ikeno, T. Yamada, Synthesis, 2004, 1434-1438.

The reaction of aliphatic and aromatic secondary and tertiary N-tritylamines with lithium powder and a catalytic amount of naphthalene led to reductive detritylation affording the corresponding amines in good yields. The trityl group could selectively be removed in the presence of an allyl or a benzyl group.
C. Behloul, D. Guijarro, M. Yus, Synthesis, 2004, 1274-1280.

Strongly complexed amines can be liberated by simple palladium and Raney nickel catalyzed methanolysis. The method is applicable to primary, secondary, tertiary and aromatic amines and tolerates various functional groups.
M. Couturier, J. L. Tucker, B. M. Andresen, P. Dube, J. T. Negri, Org. Lett., 2001, 3, 465-467.

A highly enantioselective, catalytic three-component coupling of aldehydes, alkynes, and 4-piperidone hydrochloride hydrate affords the corresponding tertiary propargylamines in useful yields. A selective cleavage of the piperidone protecting group is possible using either ammonia/EtOH or a polymer-supported scavenger amine.
P. Aschwanden, C. R. J. Stephenson, E. M. Carreira, Org. Lett., 2006, 8, 2437-2440.

Demethylation of N,N-dimethylanilines was carried out in various ionic liquids and acetonitrile as well as under solvent-free conditions. The reactivity dramatically depends on the employed solvent, with [bmim]Cl showing the best reactivity.
S. Imoria, H. Togo, Synlett, 2006, 2629-2632.