Categories: C-S Bond Formation > Synthesis of sulfones >
Synthesis of allylic sulfones
Recent Literature
Formation of allyl phenyl sulfones with excellent yields from allylic alcohols
was promoted by a combination of Pd(OAc)2, PPh3, and
Et3B via in situ activation of the alcohol group.
S. Chandrasekhar, V. Jagadeshwar, B. Saritha, C. Narsihmulu, J. Org. Chem., 2005, 70, 6506-6507.
An iridium-catalyzed allylation of various sodium sulfinates with achiral
allylic carbonates occurs in good yields, with high selectivity for the branched
isomer, and high enantioselectivities (up to 98% ee).
M. Ueda, J. F. Hartwig, Org. Lett., 2010,
12, 88-91.
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.
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.
