- Catalyst-free arylation of sulfonamidesviavisible light-mediated deamination
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A novel arylation of sulfonamides with boronic acids to afford numerous diaryl sulfonesviaa visible light-mediated N-S bond cleavage other than the typical transition-metal-catalyzed C(O)-N bond activation is described. This methodology, which represents the first catalyst-free protocol for the sulfonylation of boronic acids, is characterized by its simple reaction conditions, good functional group tolerance and high efficiency. Several successful examples for the late-stage functionalization of diverse sulfonamides indicate the high potential utility of this method in pharmaceutical science and organic synthesis.
- Ding, Hao,Ding, Qiuping,Du, Xian,Li, Yi-Hui,Liu, Bing-Zhe,Lu, Shi-Man,Luo, Yong,Qi, Wan-Ying,Xu, Xiao-Hong,Xue, Can,Yuan, Han,Zhen, Jing-Song
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p. 9556 - 9560
(2021/07/25)
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- Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions
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The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.
- Liu, Kai-Jian,Deng, Ji-Hui,Yang, Jie,Gong, Shao-Feng,Lin, Ying-Wu,He, Jun-Yi,Cao, Zhong,He, Wei-Min
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supporting information
p. 433 - 438
(2020/02/13)
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- Oxidation of aromatic sulfides with molecular oxygen: Controllable synthesis of sulfoxides or sulfones
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The recent development of selective oxidation of aromatic sulfides with molecular oxygen was highlighted. The sulfoxides and sulfones could be obtained by simply switching the reaction media, i.e., bis(2-butoxyethyl)ether (BBE) or poly(ethylene glycol)dimethyl ether (PEGDME). The application of the high-boiling-point polyether as an initiator and green media can eliminate the need of large quantities of additives and volatile solvents. This strategy represents an economic and eco-friendly method that could find potential applications.
- Tang, Lili,Du, Kejie,Yu, Bing,He, Liangnian
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p. 2991 - 2992
(2020/03/24)
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- Method for preparing aryl sulfone compound as well as method for extracting catalyst and aryl sulfone compound
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The invention provides a preparation method of an aryl sulfone compound, which is characterized in that in an organic solvent and under an aerobic atmosphere, a catalytic system composed of a metal-ligand-TEMPO is used for catalytic oxidation of a thioether compound to obtain the aryl sulfone compound. The preparation method is simple, green, and efficient, the reaction condition is mild, and theapplication range is wide; the invention also provides a method for extracting a catalyst and the product aryl sulfone compound used in the preparation process. The ethyl acetate is added to a reaction mixture, steps of filtering and condensation under reduced pressure are carried out to obtain a filtrate and the catalyst, and silica gel column chromatography and concentration extraction are carried out to obtain the aryl sulfone compound. The extraction method is simple, and the extracted catalyst has high activity and good cycle stability, and the extraction rate of the product aryl sulfonecompound is high.
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Paragraph 0076-0079
(2019/02/13)
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- A Convenient Synthesis of Sulfones via Light Promoted Coupling of Sodium Sulfinates and Aryl Halides
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A convenient and e?cient synthesis of sulfones from sulfinates and aryl halides was developed. The reaction occurred under UV irradiation without transition metal catalyst or photocatalyst. A radical pathway via single-electron transfer (SET) of electron donor-acceptor (EDA) complex was proposed based on UV-vis spectroscopy, radical inhibiting and trapping experiments. (Figure presented.).
- Chen, Lei,Liang, Jie,Chen, Zhen-yu,Chen, Jie,Yan, Ming,Zhang, Xue-jing
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p. 956 - 960
(2019/01/25)
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- Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis
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An efficient photoredox/nickel catalyzed sulfonylation reaction of aryl, heteroaryl, and vinyl halides has been achieved for the first time. This newly developed sulfonylation protocol provides a versatile method for the synthesis of diverse aromatic sulfones at room temperature and shows excellent functional group tolerance. The electrophilic coupling partners are not limited to aryl, heteroaryl, and vinyl bromides and iodides, but also includes less reactive aryl chlorides as suitable substrates for this transformation.
- Yue, Huifeng,Zhu, Chen,Rueping, Magnus
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supporting information
p. 1371 - 1375
(2018/01/27)
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- An efficient Cu-catalyzed microwave-assisted synthesis of diaryl sulfones
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An efficient and microwave-assisted simple protocol for the synthesis of symmetrical/asymmetrical diaryl sulfones through the Cu(II)-catalyzed reaction of sodium salt of sulfinic acid with aryl boronic acid has been described. Various diaryl sulfones have been synthesized in very short reaction times with moderate to very good yields. Additionally, the method is also useful for the synthesis of aryl vinyl sulfones.
- Nandi, Ganesh C.
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supporting information
p. 319 - 323
(2017/02/10)
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- First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates
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The first example of palladium-catalyzed protocol for the denitrated coupling of nitroarenes with sulfinates was developed, achieving aryl and heterocyclic sulfones in moderate to excellent yields. The cyclopalladated ferrocenylimine (I) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol %). The efficiency of this reaction was demonstrated by compatibility with a wide range of groups. Thus, the method represents a simple and facile procedure to access aryl and heterocyclic sulfones.
- Tian, Heng,Cao, Aijuan,Qiao, Lijun,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
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p. 9107 - 9112
(2015/03/05)
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- Reaction of Nucleophiles with 1,1-Dinitro-2,2-diphenylethylene
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Products of the reaction of a variety of nucleophiles with Ph2C=C(NO2)2 are reported.Michael-type adducts have been isolated: (Ph2C(N)CH(NO2)2) for N- = (RO)2PO-, (RO)2PS-, RCOCH2-.With the nucleophiles MeO- or Me2C=NO2- in Me2SO the adducts are formed but are hydrolyzed upon workup with 5percent aqueous HCl at 25 deg C to yield benzophenone.Benzophenone is also the major product from reaction with the nucleophiles NO2-, AcO-, MeC(=S)O-, EtO-, and Me3CO- in Me2SO.With N- = Me3CS-, ArS-, PhO-, or PhSe- in Me2SO, vinylic substitution occurs to yield Ph2C=C(N)NO2.With ArSO2- in DMF nucleophilic aromatic substitution occurs to yield p-ArSO2C6H4COPh.
- Russell, Glen A.,Dedolph, Douglas
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p. 3878 - 3881
(2007/10/02)
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