Categories: C-H Bond Formation >
Desulfurization
Recent Literature
A catalytic reductive cleavage of C(sp2)- and C(sp3)-SMe
bonds under ligandless conditions offers a wide scope and high chemoselectivity
profile including challenging substrate combinations, allowing the design of
orthogonal and site-selectivity approaches.
N. Barbero, R. Martin, Org. Lett., 2012,
14, 796-799.
With a molybdenum hexacarbonyl mediated desulfurization of thiols and disulfides,
sulfhydryl groups of aryl, benzyl, primary and secondary alkyl thiols, and S-S
single bonds of disulfides can be removed. This reaction tolerates many
functional groups and is not affected by steric hindrance.
Z. Wang, Y. Kuninobu, M. Kanai,
Synlett, 2014, 25, 1869-1872.
Nickel catalyzes a highly chemoselective cleavage of sp2-hybridized
carbon-sulfur bonds of readily available aryldimethylsulfonium triflates to
produce salt-free arylzinc triflates under mild conditions. The generated
arylzinc reagents show both high reactivity and chemoselectivity in
palladium-catalyzed and copper-mediated cross-coupling reactions.
K. Yamada, T. Yanagi, H. Yorimitsu, Org. Lett., 2020, 22,
9712-9718.
The reaction of 1-(methylthio)acetone with different nitriles in the
presence of triflic anhydride gave 2-substituted
5-methyl-4-methylthio-1,3-oxazoles in good yield. The methylthio group at
the C4 position can easily be removed with Raney nickel. 4-Methylsulfonyl
derivatives were prepared by the oxidation of the MeS group with m-CPBA.
A. Herrera, R. Martinez-Alvarez, P. Ramiro, D. Molero, J. Almy, J. Org.
Chem., 2006,
71, 3026-3032.