Categories: C-H Bond Formation >
Deacylations
Recent Literature
In a Cu-catalyzed degree-controlled deacylative deuteration of diverse alkyl
groups, the methylketone (acetyl) moiety acts as a traceless activating group.
The use of N-methylpicolino-hydrazonamide (MPHA) promotes efficient
aromatization-driven C-C cleavage. Mono-, di-, and trideuteration at specific
sites can be selectively achieved.
X. Zhou, T. Yu, G. Dong, J. Am. Chem. Soc.,
2022, 144, 9570-9575.
Related
A deacylative halogenation of various methyl ketones to the corresponding
alkyl chlorides, bromides, and iodides in good yields with broad FG tolerance is
driven by the formation of a 1,2,4-triazole as an aromatic byproduct. The
reaction uses N'-methylpicolinohydrazonamide to form a prearomatic
intermediate and halogen atom-transfer reagents to quench the alkyl radical
intermediates.
Z. Zhang, Q. Zhu, D. Pyle, X. Zhou, G. Dong, J. Am. Chem. Soc.,
2023, 145, 21096-21103.
A flexible metal-free cascade reaction involving aerobic C(sp3)-H
hydroxylation and decarbonylation introduces valuable secondary alcohol groups
at the α-position of N-aryl amides with high regioselectivity and
functional group tolerance.
X. Zhang, Y. Yu, W. Li, L. Shi, H. Li, J. Org. Chem., 2022, 87,
16263-16275.