- β-allyl sulfones as addition-fragmentation chain transfer reagents: A tool for adjusting thermal and mechanical properties of dimethacrylate networks
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Dimethacrylates are known to have good photoreactivity, but their radical polymerization usually leads to irregular, highly cross-linked, and brittle polymer networks with broad thermal polymer phase transitions. Here, the synthesis of mono- and difunctio
- Gorsche, Christian,Griesser, Markus,Gescheidt, Georg,Moszner, Norbert,Liska, Robert
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Read Online
- Iodosulfonylation of Alkynes under Ultrasound Irradiation
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(E)-Iodo vinylsulfones are synthesized under ultrasound irradiation using alkynes, sulfonyl hydrazides, potassium iodide and hydrogen peroxide. The key features of this protocol are the speed and efficiency of the reactions, which afford good to excellent
- Zhou, Chuanjiang,Zeng, Xianghua
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p. 4614 - 4620
(2021/09/13)
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- Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium
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A metal-free one-pot two-step synthesis of sulfonamides from readily available nitroarenes and sodium arylsulfinates in a mixture of methanol and water has been developed. In this procedure, the aryl amines were produced in situ by the reduction of nitroarenes mediated by diboronic acid, and then coupled with sodium arylsulfinates in the presence of iodine. A series of N-arylsulfonamides with various functional groups were obtained in moderate to good yields under the optimal reaction conditions. In addition, this one-pot process is applicable for gram-scale synthesis.
- Jiang, Xiaolan,Zhang, Kaili,Zhao, Rongrong,Bai, Die,Wang, Jinlong,Li, Binbin,Liu, Qixing,Zhou, Haifeng
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supporting information
(2020/09/10)
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- PROCESS FOR THE PREPARATION OF ARYLSULFONYLPROPENENITRILES BY PHOTOCATALYTIC REACTIONS
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The present invention relates to a process for the preparation of arylsulfonylpro- penenitriles. The reaction starting from arylsulfonyl iodides is catalyzed by light. The process is scalable, environmentally benign and provides the product in good yield.
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Page/Page column 10-11
(2019/03/17)
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- Copper-Catalyzed Difunctionalization of Allenes with Sulfonyl Iodides Leading to (E)-α-Iodomethyl Vinylsulfones
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A highly regioselective iodosulfonylation of allenes in the presence of CuI and 1,10-phenanthroline has been developed for the synthesis of various useful (E)-α-iodomethyl vinylsulfones in moderate to excellent yields. This practical reaction is fast, operationally simple, and in particular, proceeds under very mild conditions to afford the target products with high regio- and stereoselectivity. The selectivity was illustrated by a conceptual DFT analysis.
- Lu, Ning,Zhang, Zhiguo,Ma, Nana,Wu, Conghui,Zhang, Guisheng,Liu, Qingfeng,Liu, Tongxin
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supporting information
p. 4318 - 4322
(2018/07/29)
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- Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates
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A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N–S bond construction under mild reaction conditions.
- Reddy, Raju Jannapu,Shankar, Angothu,Waheed, Md.,Nanubolu, Jagadeesh Babu
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p. 2014 - 2017
(2018/04/25)
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- Water-Compatible Synthesis of 2-Trifluoromethyl-1,3-Dioxanes
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A water-compatible method for the diastereoselective synthesis of 2-trifluormethyl-1,3-dioxanes is described. The reaction proceeds under mild reaction conditions using simple inorganic bases; it has a very good substrate scope and can be performed with different Michael acceptors. Additionally, the reaction products can be further functionalized, showing an excellent perspective for future applications.
- Becerra-Figueroa, Liliana,Tiniakos, Alexander F.,Prunet, Jo?lle,Gamba-Sánchez, Diego
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supporting information
p. 6929 - 6932
(2018/11/25)
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- DENTAL MATERIALS WITH DEBONDING-ON-DEMAND PROPERTIES
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Radically polymerizable dental material, which contains at least one compound of Formula I: and at least one thermolabile radically polymerizable compound and/or at least one photolabile radically polymerizable compound. The materials are characterized by
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Paragraph 0093; 0094; 0095; 0096; 0097; 0103
(2017/08/01)
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- Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study
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A variety of vinyl sulfones were prepared from alkenes and sulfonyl hydrazides via electrochemical oxidative sulfonylation. The reaction proceeds in an experimentally convenient undivided electrochemical cell equipped with graphite and iron electrodes employing KI as a redox catalyst and a supporting electrolyte. Applying extremely high current density up to 270 mA/cm2 permits rapid synthesis in a compact reactor and with small surface area electrodes. A possible reaction mechanism was proposed with the use of cyclic voltammetry. It is the combination of anodic and cathodic processes in this reaction that makes it possible to obtain products under mild conditions with yields from moderate to high.
- Terent'ev, Alexander O.,Mulina, Olga M.,Pirgach, Dmitry A.,Ilovaisky, Alexey I.,Syroeshkin, Mikhail A.,Kapustina, Nadezhda I.,Nikishin, Gennady I.
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p. 6871 - 6879
(2017/11/06)
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- Iodine-catalyzed Sulfonylation of Arylacetylenic Acids and Arylacetylenes with Sodium Sulfinates: Synthesis of Arylacetylenic Sulfones
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A highly efficient and generally applicable iodine-catalyzed reaction of arylacetylenic acids and arylacetylenes with sodium sulfinates for the synthesis of arylacetylenic sulfones was developed. The methodology has the advantages of a metal-free strategy, easy to handle reagents, functional group tolerance, a wide range of arylacetylenic acids and arylacetylenes, and easy access to arylacetylenic sulfones. (Chemical Equation Presented).
- Meesin, Jatuporn,Katrun, Praewpan,Pareseecharoen, Chayaporn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Kuhakarn, Chutima
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p. 2744 - 2752
(2016/04/26)
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- Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature
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A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is
- Yang, Kai,Ke, Miaolin,Lin, Yuanguang,Song, Qiuling
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supporting information
p. 1395 - 1399
(2015/03/18)
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- An efficient one-pot, three-component synthesis of vinyl sulfones via iodide-catalyzed radical alkenylation
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An efficient one-pot, three-component synthesis of vinyl sulfones via iodide-catalyzed radical alkenylation using aryl diazonium salts, terminal alkenes and DABSO is reported. This protocol offers good yields and tolerates a broad range of functional groups. Based on the extensive control experiments, we propose a plausible radical mechanism.
- Fan, Weizheng,Su, Jiapeng,Shi, Dongyang,Feng, Bainian
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supporting information
p. 6740 - 6743
(2015/08/24)
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- Stereoselective silylcupration of conjugated alkynes in water at room temperature
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Micellar catalysis enables copper-catalyzed silylcupration of a variety of electron-deficient alkynes, thereby providing access to isomerically pure E- or Z-β-silyl-substituted carbonyl derivatives. These reactions take place in minutes, afford high yields and stereoselectivity, and are especially tolerant of functional groups present in the substrates. The aqueous reaction medium has been successfully recycled several times, and a substrate/catalyst ratio of 10,000:1 has been documented for this methodology. Fast, cheap, and green: Micellar catalysis enables the selective construction of a variety β-silyl-substituted carbonyl derivatives under mild aqueous conditions. The reaction is catalyzed by low levels of CuI, is compatible with numerous electron-withdrawing groups, affords high yields, and provides opportunities for scale-up and recycling of the reaction medium. The environmental impact, as measured by E Factors, is very low.
- Linstadt, Roscoe T. H.,Peterson, Carl A.,Lippincott, Daniel J.,Jette, Carina I.,Lipshutz, Bruce H.
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supporting information
p. 4159 - 4163
(2014/05/06)
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- Free radical addition reactions of allylic sulfones to alkenes
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Intermolecular radical reactions involving formal addition of the sulfonyl and allyl fragments of an allylic sulfone across the double bond of an alkene are described. Reactions are most successful when the allylic sulfone has an electron withdrawing group at the 2-position. Only monosubstituted alkenes give useful yields of adducts, though both electron withdrawing and electron donating substituents are effective.
- Harvey, Iain W.,Phillips, Eifion D.,Whitham, Gordon H.
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p. 6493 - 6508
(2007/10/03)
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- Cyclic enol ether synthesis via arenesulfonyl iodide additions to alkynols
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The reaction of arenesulfonyl iodides with alkynols generally provides adducts in good yields. Treatment of these adducts with KN(SiMc3)2 gives enol ethers; cyclisation of the functionalised pentenol (5) results in formation of the exo-alkylidene tetrahydrofuran (7), whereas the homologous hexenol (6) gives the dihydropyran (8). Attempts to cyclise the hexenol (6) with potassium t-butoxide under the conditions reported by Short and Ziegler generally gave the endocyclic ether (8).
- Edwards, Gavin L.,Muldoon, Craig A.,Sinclair, David J.
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p. 7779 - 7788
(2007/10/03)
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- REDUCTION OF ORGANIC SULFONIC ACIDS, SODIUM SULFONATES, AND SULFONIC ESTERS TO THE CORRESPONDING DISULFIDES WITH POLYPHOSPHORIC ACID DERIVATIVES, POTASSIUM IODIDE AND TETRABUTYLAMMONIUM IODIDE SYSTEM.
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Organic sulfonic acids, sodium sulfonates, and alkyl sulfonates were readily reduced to the corresponding disulfides in moderate yields upon treatment with a mixture of a polyphosphoric acid derivative and iodide. In these reactions, formation of mixed anhydrides each having a P-O-S linkage is the key step, and subsequent attack of iodide on the sulfur atom gives the corresponding sulfonyl iodides which are reduced further exothermally to the disulfides with the hydrogen iodide. Actually, p-toluenesulfonyl chloride was isolated in the reaction of p-toluenesulfonic acid and polyphosphoric acid derivatives with chloride ion. The competitive reduction of various aromatic sulfonic acids reveals that an aromatic sulfonic acid bearing an electron-donating para-substituent is more readily reduced to the disulfide than that which has an electron-withdrawing para-substituent.
- Oae,Togo
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p. 3813 - 3817
(2007/10/02)
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- Copper-Catalyzed Additions of Sulfonyl Iodides to Simple and Cyclic Alkenes
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A convenient synthesis for various β-iodo sulfones has been developed.The reaction involves additions of alkane- and arenesulfonyl iodides to simple and cyclic alkenes under the catalytic action of copper(II) chloride.The favored stereochemical results for cyclic alkenes have been rationalized in terms of stepwise addition of both portions of the addend from the diaxial direction.
- Liu, Lilian Kao,Chi, Y.,Jen, Kwan-Yue
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p. 406 - 410
(2007/10/02)
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