Categories: N-H Bond Formation >
Cleavage of amides
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.
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.