Categories: N-H Bond Formation >
Desulfonation
Recent Literature
Alkali metals absorbed into nanostructured silica (M-SG) were found to be useful
solid-state reagents for the desulfonation of a range of N,N-disubstituted
sulfonamides. M-SG reagents are room-temperature-stable free-flowing powders
that retain the chemical reactivity of the parent metal, decreasing the danger
and associated cost of using reactive metals.
P. Nandi, M. Y. Redko, K. Petersen, J. L. Dye, M. Lefenfeld, P. F. Vogt, J. E.
Jackson, Org. Lett., 2008,
10, 5441-5444.
A low-valent titanium generated in situ from Ti(O-i-Pr)4,
Me3SiCl, and Mg powder in THF reacted with a broad range of sulfonamides in a reductive bond
cleaving pathway to provide the corresponding amines, hydrocarbons and thiols.
The reagent could also cleave sulfonates to the corresponding alcohols.
N. Shohji, T. Kawaji, S. Okamoto, Org. Lett., 2011,
13, 2626-2629.
A convenient reductive photocleavage of sulfonamides using thioureas as
organophotocatalysts tolerates a variety of substrates and occurs under mild
reaction conditions in the presence of tetrabutylammonium borohydride as a
reducing agent.
J. Brom, A. Maruani, L. Micouin, E. Benedetti, J. Org. Chem., 2023, 88,
5923-5935.