Categories: C-S Bond Formation > Synthesis of sulfones >
Synthesis of aryl sulfones and diaryl sulfones
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A palladium-catalyzed methylsulfonylation of alkyl halides with dimethyl
sulfite enables an efficient synthesis of methyl sulfone derivatives. A variety
of aryl and alkyl iodides underwent the sulfonylation smoothly to furnish methyl
sulfones in good yields.
Y.-H. Xin, Y.-Q. Guo, X.-G. Zhang, C.-L. Deng, J. Org. Chem., 2021, 86,
17496-17503.
A simple and efficient electrochemical sulfonylation of organoboronic acids
with sodium arylsulfinate salts provides a variety of aryl, heteroaryl, and
alkenylsulfones in good yields at room temperature under catalyst- and
additive-free conditions.
W. Yao, K. Lv, Z. Xie, H. Qui, M. Ma, J. Org. Chem., 2023, 88,
2296-2305.
A metal-free and eco-friendly coupling of readily available diaryliodonium salts
and arenesulfinates in PEG-400 under microwave irradiation enables the
preparation of various diaryl sulfones in high yields and short reaction times
under mild conditions. Furthermore, the coupling of diaryliodonium with
arenesulfinate salts with and without copper iodide provides a convenient access
to various diaryl sulfones with high selectivity.
D. Kumar, V. Arun, M. Pilania, K. P. Chandra Shekar, Synlett, 2013, 24,
831-836.
An efficient and transition-metal-free synthesis of diaryl sulfones in high
yields from arylsulfinic acid salts and diaryliodonium salts tolerates a range
of functional groups and offers high chemoselectivity if unsymmetrical
diaryliodonium salts are used.
N. Umierski, G. Manolikakes, Org. Lett., 2013,
15, 188-191.
Acenaphthoimidazolylidene gold complexes are effective catalysts for a
chemoselective arylsulfonylation of boronic acids using potassium metabisulfite
(K2S2O5) and diaryliodonium salts to provide
sterically hindered diarylsulfones even in gram scale. Sterically hindered aryl
groups in unsymmetric diaryliodonium salts are preferentially transferred over
less bulky ones.
H. Zhu, Y. Shen, D. Wen, Z.-G. Le, T. Tu, Org. Lett., 2019, 21,
974-979.
A mild transition-metal-free arylation of sulfenate anions generated from
β-sulfinyl esters with diaryliodonium salts provides a wide range of S,S-diaryl
and S-alkyl S-aryl sulfoxides.
H. Yu, Z. Li, C. Bolm, Org. Lett.,
2018, 20, 7104-7106.
A fluoride triggered elimination strategy with alkyl 2-(trimethylsilyl)ethyl
sulfoxides enables a unique palladium-catalyzed arylation of alkyl sulfenate
anions to provide aryl alkyl sulfoxides in high yields. Due to the base
sensitivity of the starting sulfoxides, intermediates, and products, the use of
a mild method to generate alkyl sulfenate anions was crucial to the success of
this process.
T. Jia, M. Zhang, H. Jiang, C. Y. Wang, P. J. Walsh, J. Am. Chem. Soc., 2015,
137, 13887-13893.
FeCl3 catalyzes a solvent-free sulfonylation of arenes under
microwave irradiation. With more reactive and/or nonvolatile substrates (anisole,
xylenes, mesitylene) a short reaction time at constant MW power without control
of the temperature was used. With less reactive and/or low-boiling reagents (benzene,
toluene, halobenzenes), the MW power was controlled. A nonthermal effect was not
observed.
J. Marquié, A. Laporterie, J. Dubac, N. Roques, J.-R. Desmurs, J. Org. Chem., 2001,
66, 421-425.
In an efficient transition-metal-free synthesis of sulfones, a broad range of
alkyl/aryl/heteroaryl sodium sulfinates react with varyingly substituted o-silyl
aryl triflates as aryne precursors under mild reaction conditions to afford
structurally diverse sulfones in good to excellent yields.
V. G. Pandya, S. B. Mhaske, Org. Lett., 2014,
16, 3836-3839.
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.
A mild and efficient synthesis of diaryl sulfones from arylboronic acids and
arylsulfonyl hydrazides is described. Promoted by cupric acetate and in the
absence of additional ligand and base, the cross-coupling reaction could afford
a series of unsymmetrical diaryl sulfones in moderate to good yields at room
temperature under neutral and ambient conditions.
X.-m. Wu, Y. Wang,
Synlett, 2014, 25, 1163-1167.
Sulfonyl azides can be used as efficient sulfonyl donors. A trifluoromethanesulfonic acid-induced formation
of reactive sulfonyl cations from sulfonyl azides followed by coupling with
various arenes provides aryl sulfones at ambient temperature.
Z. Zhang, S. Wang, Y. Zhang, G. Zhang, J. Org. Chem., 2019, 84,
3919-3926.
A palladium-catalyzed arylation of aryl sulfenate anions generated from aryl
2-(trimethylsilyl)ethyl sulfoxides and CsF enables the synthesis of diaryl
sulfoxides and heteroaryl aryl sulfoxides under mild conditions employing aryl
bromides. Various functional groups are well tolerated.
T. Jia, M. Zhang, H. Jiang, C. Y. Wang, P. J. Walsh, J. Am. Chem. Soc., 2015,
137, 13887-13893.
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.
The addition of Grignard reagents or organolithium reagents to the SO2-surrogate
DABSO generates a diverse set of metal sulfinates, which can be trapped in situ
with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides,
epoxides, and (hetero)aryliodoniums to give sulfone products.
A. S. Deeming, C. J. Russell, A. J. Henessy, M. C. Willis, Org. Lett., 2014,
16, 150-153.
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.
Arynes generated in situ from 2-(trimethylsilyl)aryl triflates undergo
nucleophilic addition with thiosulfonates to produce diaryl sulfones in good
yield. The reaction can be scaled easily to gram-scale.
Y. Zheng, D. Tang, P. Xie, J. Luo, Z. Cai, L. He, Synthesis, 2023,
55,
1253-1259.
A polyaniline-graphitic carbon nitride-titanium dioxide composite catalyzes a
radical cascade reaction of an aryl diazonium salt, DABCO·(SO2)2
and 3-bromoprop-1-ene to provide aryl allyl sulfones under visible light
irradiation. A series of substrates were tolerated, providing the corresponding
products in good yields. Moreover, the photocatalyst could be readily recovered
and reused several times.
L. Wang, L.-f. Zhang, Synlett, 2022,
33,
1929-1932.
Graphitic carbon nitride (p-g-C3N4) photocatalyzes a
hydrosulfonylation of alkynes with the insertion of sulfur dioxide in aerobic
conditions. Whereas the oxygen atom of the products is derviced from water, the
O2 plays an important role by quenching the DABCO radical cation.
Furthermore, this reaction could be carried out under solar light irradiation
and was applicable for large scale.
B. Ni, B. Zhang, J. Han, B. Peng, Y. Shan, T. Niu,
Org. Lett., 2020, 22, 636-641.