Categories: N-H Bond Formation >
Cleavage of amides
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Recent Literature
The reaction of different esters, thioesters and amides derived from pivalic,
benzoic and 4-tert-butylbenzoic acids with an excess of lithium and a
catalytic amount of naphthalene led, after methanolysis, to the
corresponding alcohols, thiols and amines, respectively, through a reductive
non-hydrolytic procedure.
C. Behloul, D. Guijarro, M. Yus, Synthesis, 2006, 309-314.
La[N(TMS)2]3 catalyzes a decarbonylation and
decarbonylative hydroamination of formamides without additives. This green
protocol displays complete N-aryl/alkenyl formamide-selectivity.
S. Li, T. Rajeshkumar, J. Liu, L. Maron, X. Zhou, Org. Lett., 2023, 25,
163-168.
Transition-metal-free catalytic protocols for controlled reduction of amide
functions using cheap and bench-stable hydrosilanes as reducing agents enable
the selective reduction of unactivated C-O bonds in amides. By altering the
hydrosilane and solvent, the C-N bonds selectively breaks via a
deacylative cleavage.
W. Yao, L. He, D. Han, A. Zhong, J. Org. Chem., 2019, 84,
14627-14635.
A transacylation of N-acylsulfonamides is enabled by coincident catalytic
reactivities of FeCl3 for nonhydrolytic deacylation of N-acylsulfonamides
and subsequent acylation of the resultant sulfonamides. The reactions can be
conducted either stepwise or in a one-pot manner. These high-yielding methods
are mild, efficient, and operationally simple and tolerate a wide variety of
functional groups.
D. Sang, B. Dong, K. Yu, J. Tian, J. Org. Chem., 2024, 89,
2306-2319.