339-25-3Relevant academic research and scientific papers
Indium(III)-catalysed aryl sulfonylation reactions
Garzya, Vincenzo,Forbes, Ian T.,Lauru, Stephanie,Maragni, Paolo
, p. 1499 - 1501 (2004)
A rapid, high yielding and regioselective process has been developed for the synthesis of biaryl sulfones via sulfonylation reactions catalysed by indium(III) chloride.
Heterogeneous copper-catalyzed synthesis of diaryl sulfones
Gong, Xinchi,Qu, Lingling,Shen, Zhengqi,Wang, Ganghu,Zhu, Chunyin
, p. 10662 - 10668 (2021/12/27)
A carbon-supported copper nanoparticle (Cu-NP) with high catalytic activity for the synthesis of diaryl sulfones is reported. For the first time, this Cu-NP is proved to be able to effectively promote the reaction of arylboronic acids and arylsulfonyl hydrazides to generate diaryl sulfones at room temperature. The reaction shows excellent substrate universality, and substrates with different substituents can undergo the reaction smoothly, leading to the desired products in good yields. The Cu-NP is found to be made of low valence Cu based on XRD. Hence, the reaction catalyzed by the Cu-NP is believed to involve a Cu-mediated organometallic cycle.
Pd/NHC-catalyzed arylsulfonylation of boronic acids: A general and direct protocol to access diarylsulfones
Zhu, Haibo,Yang, Liu,Meng, Jia,Xie, Zongbo,Le, Zhang-Gao,Tu, Tao
supporting information, (2020/12/29)
For the first time, robust NHC-Pd complexes have been demonstrated as highly efficient catalysts in the direct arylsulfonylation of boronic acids. Remarkably, a broad number of diaryliodonium salts as powerful electrophilic arylation reagents are well compatible to form functional ortho-substituted diarylsulfones in satisfactory yields. Owing to the stronger σ-donor and weaker π-acceptor properties, the acenaphthoimidazolylidene ligands exhibit higher catalytic activities towards this challenging one-step arylsulfonylation reaction.
Modulation of Thermally Activated Delayed Fluorescence in Waterborne Polyurethanes via Charge-Transfer Effect
Li, Zongren,Wang, Tao,Xu, Dong,Zuo, Jie,Li, Xinyu,Li, Zhiwei,Xu, Fei,Zhang, Xingyuan
, p. 2302 - 2308 (2019/06/17)
Here, we designed several waterborne polyurethanes (WPUs) with efficient thermally activated delayed fluorescence (TADF) via serving charge-transfer (CT) states as a mediate bridge between singlet and triplet states to boost reverse intersystem crossing (RISC). By tuning substituents of diphenyl sulfone (DS), we found that O,O′- and S,S′-substituted DS covalently incorporated in WPUs solely show typical fluorescence emission with lifetimes in the nanosecond range. Interestingly, TADF appears by replacing the substituent with the nitrogen atom, of which lifetimes are up to ≈10 microseconds and ≈1 millisecond in air and vacuum, respectively, even though the energy gap between singlet and triplet states (ΔEST) is still large for generating TADF. To explain this phenomenon, an energy level mode based on CT states and an 3(n-π*) receiver state was proposed. By the rational modulation of CT states, it is possible to tune the ΔEST to render TADF-based materials suitable for versatile applications.
Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: Synthesis of (un)symmetrical diaryl/alkyl aryl sulfones
Chawla, Ruchi,Yadav, Lal Dhar S.
supporting information, p. 4761 - 4766 (2019/05/24)
We disclose herein the first transition-metal-and external oxidant/reductant-free visible-light-mediated synthesis of (un)symmetrical diaryl/alkyl aryl sulfones from arenediazonium tetrafluoroborates and sodium sulfinates using eosin Y as an organic photoredox catalyst. The utilization of visible light as an inexpensive and ecosustainable energy source, operational simplicity, ambient temperature and clean reaction in aqueous acetonitrile are the salient features of the developed protocol. The desired sulfones were also synthesized via a one-pot, two-step process directly from anilines and sulfinate salts in good to excellent yields.
Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions
Zhu, Haibo,Shen, Yajing,Wen, Daheng,Le, Zhang-Gao,Tu, Tao
supporting information, p. 974 - 979 (2019/02/14)
A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K2S2O5) and diaryliodonium salts to access (poly-)ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal-catalyzed two-component coupling systems, the sterically hindered aryl groups in diaryliodonium salts are preferentially transferred over less bulky ones to form synthetically difficult targets, including those of pharmaceutical importance.
Visible-Light-Driven Silver-Catalyzed One-Pot Approach: A Selective Synthesis of Diaryl Sulfoxides and Diaryl Sulfones
Kim, Dong Hyuk,Lee, Juyoung,Lee, Anna
supporting information, p. 764 - 767 (2018/02/09)
An efficient one-pot approach for the synthesis of diaryl sulfoxides and diaryl sulfones using aryl thiols and aryl diazonium salts was developed. The use of a visible-light-driven silver catalysis and the subsequent singlet-oxygen-induced oxidation enabled selective synthesis of sulfoxides and sulfones in the absence of a photocatalyst. The reactions were carried out under mild reaction conditions; the desired products were obtained under air atmosphere at room temperature.
Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides
Liu, Nai-Wei,Hofman, Kamil,Herbert, André,Manolikakes, Georg
supporting information, p. 760 - 763 (2018/02/09)
An efficient cross-coupling of sodium or lithium sulfinates with aryl iodides, using a combination of nickel and photoredox catalysis, is described. The dual catalyst system enables a versatile synthesis of aryl sulfones at room temperature in good yields and displays a broad functional group compatibility. The potential utility of this method in the late-stage diversification of complex molecules and in the conversion of organolithium reagents and sulfur dioxide into sulfones is demonstrated.
Preparation process of fluorine substituted aromatic compound
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, (2008/06/13)
A preparation process of a fluorine substituted aromatic compound comprising reacting an alkali metal or alkali earth metal salt of an aromatic compound having a hydroxy group with an organic fluorinating agent is disclosed. As a representative fluorinating agent, a bis-dialkylamino-difluoromethane compound, for example, 2,2′-difluoro-1,3-dimethylimidazolidine, is exemplified. According to the process, an industrially useful fluorinated aromatic compound, for example, a fluorobenzene, a fluorine substituted benzophenone, a fluorine substituted diarylsulfone can be prepared with ease in economy without specific equipment.
