Categories: C-S Bond Formation > Synthesis of sulfones >
Synthesis of aryl sulfones and diaryl sulfones
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A simple, mild and efficient method for the synthesis of unsymmetrical
diaryl sulfones using the palladium-catalyzed coupling of aryl boronic acids
and arylsulfonyl chlorides has been developed.
B. P. Bandgar, S. V. Bettigeri, J. Phopase, Org. Lett., 2004, 6, 2105-2108.
A mild and efficient copper-catalyzed cross-coupling reaction of arylboronic
acids with sulfinic acid salts affords a wide range of alkylaryl and diaryl
sulfones in good yields under ambient conditions. The use of an ionic liquid
allows a convenient separation of the product and recycling of copper catalyst.
M. L. Kantam, B. Neelima, B. Sreedhar, R. Chakravarti, Synlett, 2008,
1455-1458.
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.
