Categories: C-S Bond Formation > Synthesis of sulfones >
Synthesis of benzylic sulfones
Recent Literature
In the absence of external catalysts and additives, a broad range of benzylic
and allylic alcohols react with various sulfinyl chlorides to afford
structurally diversified benzylic and allylic sulfones in moderate to excellent
yields. A catalysis with byproduct HCl is involved in this new protocol.
H.-H. Li, D.-J. Dong, Y.-H. Jin, S.-K. Tian, J. Org. Chem., 2009,
74, 9501-9504.
A palladium complex generated in situ from [Pd(η3-C3H5)Cl]2 and DPEphos
[bis(2-diphenylphosphinophenyl)ether] catalyzed the nucleophilic substitution of benzylic carbonates with sodium
arenesulfinates in DMSO at 80°C. The
reaction gave a variety of benzylic sulfones in
high yields.
R. Kuwano, Y. Kondo, T. Shirahama, Org. Lett., 2005, 7, 2973-2975.
A one-pot synthesis of aryl sulfones from primary alcohols is described.
Alcohols were treated with N-bromosuccinimide and triphenylphosphine,
followed by addition of sodium arenesulfinate with a catalytic amount of
tetrabutylammonium iodide to afford the aryl sulfones in good to high yields.
T. Murakami, K. Furusawa, Synthesis, 2002, 479-482.
