Categories: C-S Bond Formation > Synthesis of sulfones >
Vinyl sulfones
Recent Literature
Alkenyl sulfones can be stereoselectively synthesized from alkenes or alkynes
using sodium sulfinates in the presence of CuI-bpy as catalyst and oxygen. The
reaction of alkenes gives (E)-alkenyl sulfones via anti addition
of the sulfonyl cation followed by an elimination process. Furthermore, the
employment of alkynes produces (E)-β-haloalkenyl sulfones in the presence
of potassium halides.
N. Taniguchi, Synlett, 2011,
1308-1312.
The palladium-catalyzed reaction of sulfinic acid salts with a wide variety
of aryl and vinyl halides or triflates, which is strongly influenced by the
presence of nBu4NCl, provides unsymmetrical diaryl
sulfones and aryl vinyl sulfones in good yields. The use of Xantphos, a
rigid bidentate ligand with a wide natural bite angle, was found to be
crucial for the success of the reaction.
S. Cacchi, G. Fabrizi, A. Goggiamani, L. M. Parisi, R. Bernini, J. Org.
Chem., 2004, 69, 5608-5614.
An easily accessible, anion-functionalized ionic liquid,
1-ethyl-3-methylimidazolium (S)-2-amino-3-methylbutyric acid salt, [emim][Val],
is an efficient additive for the CuI-catalyzed coupling reaction of sulfinic
acid salts with aryl iodides, aryl bromides and vinyl bromides, leading to
sulfones in good yields.
M. Bian, F. Xu, C. Ma, Synthesis, 2007,
2951-2956.
Using [Ir(COD)Cl]2 and a phosphoramidite ligand in the
presence of DBU, trisubstituted vinyl sulfones could be synthesized from allyl
sulfinates in high yields as exclusively E isomers.
Q.-L. Xu, L.-X. Dai, S.-L. You, Org. Lett., 2010,
12, 800-803.
An efficient synthesis of vinyl sulfones with commercially available sulfinic acid sodium salts
and dibromides gave various phenyl and methyl vinyl sulfones in
good yields, in the absence of any catalyst.
Z.-H. Guan, W. Zuo, L.-B. Zhao, Z.-H. Ren, Y.-M. Liang, Synthesis, 2007,
1465-1470.
An efficient synthesis of vinyl sulfones with commercially available sulfinic acid sodium salts
and dibromides gave various phenyl and methyl vinyl sulfones in
good yields, in the absence of any catalyst.
Z.-H. Guan, W. Zuo, L.-B. Zhao, Z.-H. Ren, Y.-M. Liang, Synthesis, 2007,
1465-1470.
The cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates
and sodium iodide with alkenes afforded vinyl sulfones in very good yields.
Alkynes underwent a similar reaction to give β-iodovinyl sulfones, which on
treatment with potassium carbonate afforded the corresponding acetylenic
sulfones in high yields.
V. Nair, A. Augustine, T. D. Suja, Synthesis, 2002, 2259-2265.
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