66-39-7Relevant academic research and scientific papers
Ceramic boron carbonitrides for unlocking organic halides with visible light
Yuan, Tao,Zheng, Meifang,Antonietti, Markus,Wang, Xinchen
, p. 6323 - 6332 (2021/05/19)
Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is
Hantzsch Ester as a Visible-Light Photoredox Catalyst for Transition-Metal-Free Coupling of Arylhalides and Arylsulfinates
Zhu, Da-Liang,Wu, Qi,Li, Hai-Yan,Li, Hong-Xi,Lang, Jian-Ping
supporting information, p. 3484 - 3488 (2020/03/05)
Diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (HEH) has been utilized as a visible-light photoredox catalyst for the cross coupling of arylhalides and arylsulfinates without transition metal, sacrificial agent, and mediator. This method is compatible with various functional groups and provides diaryl sulfones in good to high yields. Mechanistic studies indicate that this reaction undergoes the stepwise light irradiation of HE?, single electron transfer (SET) in donor–acceptor complex (DAC) from *HE? to arylhalide, trapping of aryl radical with sulfinate, and SET oxidation of sulfone radical anion by HE. to sulfone by the DAC method.
Mo(VI) complex catalysed synthesis of sulfonees and their modification for anti-HIV activities
Madduluri, Vimal Kumar,Baig, Noorullah,Chander, Subhash,Murugesan, Sankaranarayanan,Sah, Ajay K.
, (2020/01/23)
An efficient method for the synthesis of sulfones has been developed using sugar derived cis-dioxo molybdenum(VI) complex as catalyst and urea hydrogen peroxide as oxygen source. Present method is highly specific for sulfide oxidation irrespective of presence of alkene and aldehyde groups in the same molecule. Synthesis of fifteen sulfones have been reported with 82–98% isolated yields and the catalyst has been reused five times without any loss in its activity. 2-(Phenylsulfonyl)aniline has been condensed with eight different aromatic aldehydes and the products are being explored for HIV-1 reverse transcriptase inhibition activities.
Nickel-Catalyzed Synthesis of Diaryl Sulfones from Aryl Halides and Sodium Sulfinates
Liu, Nai-Wei,Liang, Shuai,Margraf, Natalie,Shaaban, Saad,Luciano, Vanessa,Drost, Marcella,Manolikakes, Georg
supporting information, p. 1208 - 1210 (2018/03/21)
A novel nickel-catalyzed cross-coupling of sulfinic acid salts with aryl halides is described. The reaction provides access to various diaryl sulfones in moderate to excellent yields. A broad range of functional groups and heteroaromatic compounds is tolerated under the reaction conditions.
Engaging sulfinate salts via Ni/photoredox dual catalysis enables facile Csp2-SO2R coupling
Cabrera-Afonso, María Jesús,Lu, Zhi-Peng,Kelly, Christopher B.,Lang, Simon B.,Dykstra, Ryan,Gutierrez, Osvaldo,Molander, Gary A.
, p. 3186 - 3191 (2018/03/30)
This report details the development and implementation of a strategy to construct aryl- and heteroaryl sulfones via Ni/photoredox dual catalysis. Using aryl sulfinate salts, the C-S bond can be forged at room temperature under base-free conditions. An array of aryl- and heteroaryl halides are compatible with this approach. The broad tolerance and mild nature of the described reaction could potentially be employed to prepare sulfones with biological relevance (e.g., in bioconjugation, drug substance synthesis, etc.) as demonstrated in the synthesis of drug-like compounds or their precursors. When paired with existing Ni/photoredox chemistry for Csp3-Csp2 cross-coupling, an array of diverse sulfone scaffolds can be readily assembled from bifunctional electrophiles. A mechanistic manifold consistent with experimental and computational data is presented.
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.
Derivative of tetra-substituted pyrrolo [3,2-b] pyrrole and organic electroluminescence device based on same
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Paragraph 0039; 0040, (2017/05/18)
The invention provides a derivative of 2,5-substituted 1,4-di(4-tert-butyl-phenyl) pyrrolo [3,2-b] pyrrole, and application of the derivative. The derivative has the following structural formula as shown in the specification; in the formula, R represents
An efficient Cu-catalyzed microwave-assisted synthesis of diaryl sulfones
Nandi, Ganesh C.
supporting information, p. 319 - 323 (2017/02/10)
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.
OXACAZONE COMPOUNDS TO TREAT CLOSTRIDIUM DIFFICILE
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Page/Page column 110, (2016/04/04)
Compounds, compositions, and methods for treating C. difficile are provided.
First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates
Tian, Heng,Cao, Aijuan,Qiao, Lijun,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
, p. 9107 - 9112 (2015/03/05)
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.
