6311-65-5Relevant academic research and scientific papers
Sulfoxylate Anion Radical-Induced Aryl Radical Generation and Intramolecular Arylation for the Synthesis of Biarylsultams
Laha, Joydev K.,Gupta, Pankaj
, p. 4204 - 4214 (2022/03/16)
Aryl radical generation from the corresponding aryl halides using an electron donor and subsequent intramolecular cyclization with arenes could be an important advancement in contemporary biaryl synthesis. A green and practically useful synthetic protocol to access diverse six- and seven-membered biarylsultams especially with a free NH group including demonstration of a gram-scale synthesis is reported herein. The sulfoxylate anion radical (SO2-?), generated in situ from the reagents rongalite or sodium dithionite (Na2S2O4), was found to be the key single electron transfer agent forming aryl radicals from aryl halides, which upon intramolecular arylation gives biarylsultams with good to excellent yields. The approach features generation of aryl radicals that remained underexplored, use of a cheap and readily available industrial reagents, and transition metal-free, mild, and green reaction conditions.
Copper-Catalyzed Aminoarylation of Alkenes via Aminyl Radical Addition and Aryl Migration
Wang, Jin-Lin,Liu, Mei-Ling,Zou, Jian-Yu,Sun, Wen-Hui,Liu, Xue-Yuan
supporting information, p. 309 - 313 (2022/01/04)
We describe a new strategy for aminoarylation of alkenes by copper-catalyzed smiles rearrangement using O-benzoylhydroxylamines as the amine reagent. This method affords various β-amino amide derivatives possessing a quaternary carbon center with wide functional group tolerance and high regioselectivity. The mechanistic studies indicate that the transformation can involve aminyl radical intermediates under acid-free condition.
Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides
Ahmadpoor, Fatemeh,Nasrollahzadeh, Mahmoud,Nezafat, Zahra,Pakzad, Khatereh
, (2021/06/25)
The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.
Sulfonamide compound and metal-free catalytic construction method and application thereof
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Paragraph 0046-0050, (2020/07/21)
The invention discloses a sulfonamide compound as shown in a formula (I) which is described in the specification and a synthesis method thereof. A series of sulfonamide compounds are obtained throughreaction of nitroaromatic hydrocarbon, an inorganic sulfur reagent and boric acid as reaction raw materials in a solvent under the action of alkali and an additive. Metal catalysis and an additional reducing agent are not needed, an inorganic sulfur reagent is used as a sulfur source and a reducing agent, and a series of sulfonamide compounds are constructed in one step by a three-component one-pot method. The invention also discloses an application of the sulfonamide compound in synthesis of sulfonamide drugs. The raw materials of the synthesis method are wide in source, cheap and easy to obtain; the reaction operation is simple; the substrate universality is high; and the synthesis method is economic and practical. The sulfonamide compound has high practical value and a wide applicationprospect.
Straightforward Sulfonamidation via Metabisulfite-Mediated Cross Coupling of Nitroarenes and Boronic Acids under Transition-Metal-Free Conditions?
Li, Yaping,Wang, Ming,Jiang, Xuefeng
supporting information, p. 1521 - 1525 (2020/09/09)
A straightforward multicomponent sulfonamidation of nitroarenes, sodium metabisulfite and boronic acids was established under transition-metal-free conditions to access diverse sulfonamides from readily available and low-cost materials modularly. Inorganic salt sodium metabisulfite not only served as a sulfur dioxide source, but also played a key role for both activator and reductant during sulfonamidation. Notably, naturally occurring biomolecules and pharmaceuticals with multiple heteroatoms and sensitive functional groups were intensively investigated in this transformtion providing versatile sulfonamides collectively. Further mechanistic studies demonstrated that nitrosoarene is the key intermediate, and the activation of boronic acid is the rate-determining step in the transformation.
Sequential C-S and S-N Coupling Approach to Sulfonamides
Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
supporting information, p. 1841 - 1845 (2020/03/04)
A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.
Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates
Liu, Saiwen,Chen, Ru,Zhang, Jin
, (2019/05/02)
A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.
Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound
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Paragraph 0037-0041, (2019/11/12)
The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.
Multicomponent synthesis of sulfonamides from triarylbismuthines, nitro compounds and sodium metabisulfite in deep eutectic solvents
Marset, Xavier,Torregrosa-Crespo, Javier,Martínez-Espinosa, Rosa M.,Guillena, Gabriela,Ramón, Diego J.
supporting information, p. 4127 - 4132 (2019/08/07)
A sustainable synthesis of sulfonamides using a copper-catalysed process starting from triarylbismuthines, Na2S2O5 and nitro compounds in a Deep Eutectic Solvent (DES) as a reaction medium is described. Thus, triarylbismuthines are used as reagents for the incorporation of SO2 into organic motifs. The bismuth salts formed as by-products can be easily removed from the crude reaction mixture by precipitation with water, while the use of volatile organic compounds (VOCs) as solvents can be avoided in the entire process. The eutectic mixture employed as the solvent is fully characterised, with the preliminary results proving its low toxicity. The designed DES also allows for a novel multicomponent reaction which saves time and reduces purification steps, energy and cost.
Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines
Dong, Wanrong,Liu, Chaoyang,Ma, Xinchi,Zhang, Yingjun,Peng, Zhihong,Xie, Dexun,An, Delie
, p. 3886 - 3893 (2019/06/18)
A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on the results of control reactions and EPR analysis.
