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Cleavage of amides

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IBX promotes a highly selective oxidative cleavage of inert C(aryl)-N bonds on secondary amides while leaving the C(carbonyl)-N bond unchanged. This metal-free reaction proceeds under mild conditions and provides facile access to various useful primary amides.
Z. Zhang, D. Zheng, Y. Wan, G. Zhang, J. Bi, Q. Liu, Q. Liu, T. Liu, L. Shi, J. Org. Chem., 2018, 84, 1369-1376.


Cu(acac)2 catalyzes an unprecedented N-demethylation of N-methyl amides in the presence of N-fluorobenzenesulfonimide as an oxidant. The reaction involves carbinolamines as intermediates, that spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
X. Yi, S. Lei, W. Liu, F. Che, C. Yu, X. Liu, Z. Wang, X. Zhou, Y. Zhang, Org. Lett., 2020, 22, 4583-4587.


A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Reactions of RhCl3 with n-PrOH provide an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides and generate a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.
M. J. Zacuto, F. Xu, J. Org. Chem., 2007, 72, 6298-6300.