14156-61-7Relevant academic research and scientific papers
Synthesis of Aromatic Sulfones from SO2 and Organosilanes Under Metal-free Conditions
von Wolff, Niklas,Char, Jo?lle,Frogneux, Xavier,Cantat, Thibault
, p. 5616 - 5619 (2017)
The conversion of SO2 into arylsulfones under metal-free conditions was achieved for the first time by reacting SO2 with (hetero)arylsilanes and alkylhalides in the presence of a fluoride source. The mechanism of this transformation was elucidated based on DFT calculations, which highlight the influence of SO2 in promoting C?Si bond cleavage.
Sulfonylation from sodium dithionite or thiourea dioxide
He, Fu-Sheng,Yang, Min,Ye, Shengqing,Wu, Jie
, p. 461 - 464 (2020/06/03)
The cheap and easily available sodium dithionite and thiourea dioxide have been used as the source of sulfonyl group in the synthesis of sulfones and sulfonamides recently. Compared with other methods for the sulfonylation reactions, the strategies using sodium dithionite or thiourea dioxide provide an alternative and complementary route to diverse sulfonyl compounds. During the reaction process, sulfur dioxide anion radical is the key intermediate, which is usually generated from a single electron transfer under suitable conditions. The advantages using sodium dithionite or thiourea dioxide in the sulfonylation reactions include mild conditions and broad substrate scope with excellent functional group compatibility. Further applications by using sodium dithionite and thiourea dioxide in organic transformations will be anticipated.
Catalyst-Free Sulfonylation of (Hetero)aryl Iodides with Sodium Dithionite
Li, Yuewen,Liu, Tong,Qiu, Guanyinsheng,Wu, Jie
supporting information, p. 1154 - 1159 (2019/01/30)
The commercially available and cheap sodium dithionite is used as the source of sulfonyl group for the synthesis of sulfones and sulfonamides from (hetero)aryl iodides under catalyst-free conditions. During the reaction process, sodium sulfinates generated in situ are the key intermediate, which can be further converted into diverse sulfones and sulfonamides. This transformation proceeds through a radical process initiated by sodium dithionite, providing a convenient route to sulfonyl-containing compounds. (Figure presented.).
Oxidative kinetic resolution of heterocyclic sulfoxides with a porphyrin-inspired manganese complex by hydrogen peroxide
Yang, Jinchuang,Wang, Lianyue,Lv, Ying,Li, Ning,An, Yue,Gao, Shuang
supporting information, p. 156 - 159 (2017/12/15)
We have successfully reported here the low loading porphyrin-inspired high-valent manganese (IV)-oxo complex was applied in oxidative kinetic resolution (OKR) of racemic heterocyclic sulfoxides using the environmentally benign hydrogen peroxide for the first time. This approach allows for rapid OKR (0.5 h) of a variety of racemic sulfoxides (including pyridine, pyrimidine, pyrazine, thiazole, benzothiazole, thiophene) in excellent enantioselectivity (up to > 99% ee), simultaneously generating the corresponding sulfones in high yield (up to 80%). The catalytic system also showed an unexceptionable chemoselectivity for the sulfoxide substrates with hydroxyl groups in which only the sulfoxide group was oxidized. The practical utility of the method has been demonstrated in the OKR of gram-scale sulfoxides.
Process for the Synthesis of Sulfones and Sulfonamides
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Paragraph 0268; 0269; 0270; 0271; 0272, (2017/07/06)
A one pot single step process is described for the synthesis of a compound, including a labeled compound, containing a sulfonyl functional group comprising the step of mixing together a silane, an SO2 source, an electrophilic compound, an activ
Palladium-Catalyzed Remote ortho-C-H Alkenylation of Alkyl Aryl Sulfones: Access to Densely Functionalized Indane Derivatives
Legarda, Pablo D.,García-Rubia, Alfonso,Gómezarrayás, Ramón,Carretero, Juan C.
supporting information, p. 1065 - 1072 (2016/04/19)
A practical method for the palladium-catalyzed ortho-olefination of benzyl and phenethyl 2-pyridyl sulfones with electron-deficient alkenes using N-fluoro-2,4,6-trimethylpyridinium triflate ([F+]) as the terminal oxidant is described. The chela
Sulphonamido-Substituted Cyclohexyl Sulphones for Treatment of Cancer
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, (2009/09/07)
Compounds of formula (I) are disclosed for treatment of cancer.
4-chloro-3,5-dimethyl-2-sulfonyl pyridines
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Example 7, (2010/11/29)
2-Sulfonylpyridine derivatives can be industrially produced efficiently by reacting a sulfonyl cyanide derivative with an α,β-unsaturated carbonyl compound and a 2-{[(2-pyridyl)methyl]thio}-1H-benzimidazole skeleton can be formed in one step in a good yield by reacting this type of the 2-sulfonylpyridine derivative with a 2-methylthio-1H-benzimidazole derivative in the presence of an organolithium compound.
Stereochemistry of direct olefin formation from carbonyl compounds and lithiated heterocyclic sulfones
Baudin, J. B.,Hareau, G.,Julia, S. A.,Lorne, R.,Ruel, O.
, p. 856 - 878 (2007/10/02)
The conditions for the title reaction were studied for the 2-benzothiazole and 2-pyridine series and for some examples in the 2-pyrimidine series.The olefin preparations were generally observed to be more efficient for 2-BT-sulfone systems.From the data of the hundred cases studied, it can be concluded that (E)-olefins are obtained: (i) from saturated BT-sulfones and aromatic aldehydes; and (ii) from benzylic BT-sulfones and branched saturated aldehydes (isobutyraldehyde, pivalaldehyde) or α,β-ethylenic or aromatic aldehydes. (Z)-olefins arise: (i) fom propargylic BT-sulfones and saturated or aromatic aldehydes; and (ii) from allylic or benzylic Pyr-sulfones and saturated aldehydes.Possible mechanisms for this new olefination procedure were examined. - heteroaromatic sulfones, organolithium derivatives, intramolecular ipso reactions, stereochemistry, elimination, olefination.
A CONVENIENT AND GENERAL SYNTHESIS OF ALKANE SULFINIC ACIDS
Ueno, Yoshio,Kojima, Akihiko,Okawara, Makoto
, p. 2125 - 2128 (2007/10/02)
2-(Alkylsulfonyl)benzothiazoles are reduced with sodium tetrahydroborate to give alkane sulfinic acids in good yield.
