- Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides
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Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.
- Yi, Dong,He, Linying,Qi, Zhongyu,Zhang, Zhijie,Li, Mengshun,Lu, Ji,Wei, Jun,Du, Xi,Fu, Qiang,Wei, Siping
-
supporting information
p. 859 - 865
(2021/03/04)
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- Photosensitizer-free synthesis of β-keto sulfones: Via visible-light-induced oxysulfonylation of alkenes with sulfonic acids
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A practical and environment-friendly methodology for the construction of β-keto sulfones through visible-light induced direct oxysulfonylation of alkenes with sulfonic acids at ambient temperature under open-air conditions was developed. Most importantly, the reaction proceeded smoothly without the addition of any photocatalyst or strong oxidant, ultimately minimizing the production of chemical waste.
- Hong, Yun-Yun,Peng, Sha,Peng, Zhen,Tang, Shan-Shan,Xie, Long-Yong,Xu, Xiang-Qun,Yang, Li-Hua
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supporting information
p. 4537 - 4541
(2021/05/31)
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- Copper-catalyzed aerobic oxidative cross-coupling reactions of vinylarenes with sulfinate salts: A direct approach to β-ketosulfones
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A copper-catalyzed aerobic oxidative cross-coupling reactions for the synthesis of β-ketosulfones via formation of a C[sbnd]S bond has been demonstrated. Promoted by the crucial copper catalyst, perfect selectivity and good to excellent yields could be achieved. This method, including inexpensive copper catalyst, wide functional group tolerance, and open air conditions, make it very attractive and practical. More importantly, it also provides a versatile tool for the construction of β-ketosulfones from basic starting materials under mild conditions.
- Chen, Yu,Xu, Lei,Wang, Biyu,Jiang, Jingjing,Sun, Yixiang,Li, Longchun
-
-
- Dioxygen-Triggered Oxosulfonylation/Sulfonylation of Terminal Olefins toward β-Keto Sulfones/Sulfones
-
A dioxygen-triggered oxosulfonylation/sulfonylation of unactivated olefins to achieve β-keto sulfones/sulfones has been developed. Interestingly, pluralistic mechanisms were found when different types of compounds were applied as substrates, and different products were achieved. The reaction is carried out with a high atomic efficiency in the absence of a metal and a catalyst at room temperature under an air atmosphere. Importantly, as a proof-of-concept, a bioactive molecule was synthesized on a gram-scale level using this method.
- Wang, Yanjie,Zhao, Yuhan,Cai, Changqun,Wang, Lingyun,Gong, Hang
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supporting information
p. 8296 - 8301
(2021/11/13)
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- Electrochemical Sulfonylation of Alkynes with Sulfonyl Hydrazides: A Metal- and Oxidant-Free Protocol for the Synthesis of Alkynyl Sulfones
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Herein, an electrochemical oxidative cross-coupling reaction between terminal alkynes and sulfonylhydrazides has been developed. Tetrabutylammonium iodide is used as the electrolyte and redox medium. The significant advantages of this method are high atom efficiency, functional group tolerance, and transition metal- and oxidant-free conditions. Most of the compounds exhibit good inhibitory activity on tumor cell lines, and one of the compounds can inhibit cell migration and induce apoptosis in HeLa cells. (Figure presented.).
- Mo, Zu-Yu,Zhang, Yu-Zhen,Huang, Guo-Bao,Wang, Xin-Yu,Pan, Ying-Ming,Tang, Hai-Tao
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p. 2160 - 2167
(2020/03/04)
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- Biomimetic photocatalytic sulfonation of alkenes to access β-ketosulfones with single-atom iron site
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Biomimetic photocatalysis as an important organic transformation strategy has received increasing attention, with the performances of biomimetic catalysts largely depending on their design. This protocol has been initially used to fabricate a biomimetic photocatalyst of single-atom iron site through coupling carbon nitride with hemin (CNH) for the visible light-promoted sulfonation of alkenes to produce β-ketosulfones with up to 94% yield. The experimental results show that the role of CN in CNH is concentrated on enhancing the separation ability of photogenerated electron pairs and holes to improve the photocatalytic activity and stability. Moreover, the as-prepared photocatalyst of single atom iron can be irradiated under near-infrared light with a satisfactory yield, and is also feasible for the sulfonation reactions of androstenones. Importantly, this biomimetic catalysis-based synthesis system has some merits, namely high catalysis efficiency, favorable recyclability, high turnover number, and excellent functional group tolerance, making it promising for extensive applications in organic transformations for the synthesis of β-ketosulfones to access various bioactive drugs.
- Wen, Jiangwei,Yang, Xiaoting,Sun, Zongzhao,Yang, Jianjing,Han, Ping,Liu, Qiuxia,Dong, Hongyan,Gu, Meng,Huang, Limin,Wang, Hua
-
supporting information
p. 230 - 237
(2020/01/21)
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- A Naphthalimide-Based ND-O-EAc Photocatalyst for Sulfonation of Alkenes to Access β-Ketosulfones Under Visible Light
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The development of facile, efficient, cost-effective, and visible light-driven photocatalysts for organic synthetic chemistry has received increasing attention. This protocol has initially synthesized a naphthalimide-based ND-O-EAc visible light photocatalyst for the sulfonation of alkenes to produce β-ketosulfones. Compared with the current photosynthetic strategies, the newly developed catalytic system has some merits, namely high efficiency, gram-scale preparation of low-cost photocatalyst, no metal contamination, wide substrate scope, and green terminal oxidant of air. Moreover, the prepared photocatalyst of ND-O-EAc is feasible for the sulfonation reactions of androstenones. Importantly, such a photocatalysis strategy can easily realize the scale-up synthesis for β-ketosulfone drugs under the mild conditions up to 90 % yield.
- Yang, Xiaoting,Yang, Jianjing,Yan, Kelu,Qin, Hongyun,Dong, Wenjie,Wen, Jiangwei,Wang, Hua
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supporting information
p. 3456 - 3461
(2020/06/08)
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- Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro
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Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.
- Iqbal Choudhary, M.,Iqbal, Sarosh,Khan, Ajmal,Khan, Khalid Mohammed,Kiran, Shumaila,Nazir, Rashid,Perveen, Shahnaz
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p. 244 - 255
(2020/03/10)
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- Sulfated tungstate/dioxygen: A new catalytic system for oxysulfonylation of styrenes to form β-keto sulfones
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A new system for synthesis of a wide range of β-keto sulfones using sulfated tungstate as a heterogeneous catalyst and oxygen as an environmentally benign oxidant with aryl hydrazides and styrenes as reacting counterparts has been developed. The preliminary experimental results support the involvement of free radical species. Thus, aryl sulfonyl free radicals, generated by oxidation of aryl sulfonyl hydrazides, subsequently undergo a tandem addition to styrenes to form intermediate benzyl free radicals, and oxygen capture and oxidation to furnish β-keto sulfones. The method is mild and efficient with easy workup procedures. The catalyst is recyclable. This journal is
- Akamanchi, Krishnacharya G.,Autade, Snehalata B.,Kulkarni, Raghavendra V.,Wagh, Ganesh D.
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p. 10554 - 10561
(2020/07/14)
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- Heterogeneous copper-catalyzed oxidative coupling of oxime acetates with sodium sulfinates: An efficient and practical synthesis of β-keto sulfones
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An efficient and practical route to β-keto sulfones has been developed through heterogeneous oxidative coupling of oxime acetates with sodium sulfinates by using an MCM-41-supported Schiff base-pyridine bidentate copper (II) complex [MCM-41-Sb,Py-Cu (OAc)2] as the catalyst and oxime acetates as an internal oxidant, followed by hydrolysis. The reaction generates a variety of β-keto sulfones in good to excellent yields. This new heterogeneous copper (II) catalyst can be easily prepared via a simple procedure from readily available and inexpensive reagents and exhibits the same catalytic activity as Cu (OAc)2. MCM-41-Sb,Py-Cu (OAc)2 is also easy to recover and is recyclable up to eight times with almost consistent activity.
- Xia, Jianhui,Huang, Xue,You, Shengyong,Cai, Mingzhong
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-
- Cu-doped zeolitic imidazolate framework catalysed highly selective conversion of alkynes to β -keto and vinyl sulfones using sodium sulfinates
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Abstract: Cu 2 +-doped zeolitic imidazolate framework-8 (ZIF-8)-catalyzed one-pot procedure to synthesize β -keto and vinyl sulfones by the direct oxysulfonylation and hydrosulfonylation of alkynes via radical reaction under mild conditions has been described. The advantages of this protocol included broad substrate scope and excellent β -keto and E-stereoselectivity. The Cu/ZIF-8 catalyst not only exhibited excellent performance but also had a great stability in the reaction, successfully allowing its reuse up to five cycles. This efficient Cu/ZIF-8 heterogeneous catalyst is explored for the first time to generate β -keto and vinyl sulfones. Graphical Abstract:: Cu 2 +-doped zeolitic imidazolate framework-8 (ZIF-8)-catalyzed one-pot procedure to synthesize β -keto and vinyl sulfones by the direct oxysulfonylation and hydrosulfonylation of alkynes via radical reaction under mild conditions is described. The advantages of this protocol included broad substrate scope and excellent β -keto and E-stereoselectivity. This efficient Cu/ZIF-8 heterogeneous catalyst is explored for the first time for C-S bond formation. [Figure not available: see fulltext.].
- Yalavarthi, Nageswara Rao,Gundoju, Narayanarao,Bokam, Ramesh,Ponnapalli, Mangala Gowri
-
-
- One-pot synthesis of chiral β-hydroxysulfones from alkynes: Via aerobic oxysulfonylation and asymmetric reduction in MeOH/H2O
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A highly enantioselective synthesis of β-hydroxysulfones from inexpensive and readily available terminal alkynes and sodium sulfinates via a consecutive one-pot reaction in an aqueous medium under mild conditions is described. The intermediates, β-keto sulfones, generated from an aerobic oxysulfonylation of terminal alkynes and sodium sulfinates catalyzed by an iron salt in MeOH/H2O (v : v = 3 : 1) at 50 °C, were subsequently reduced by a Ru-catalyzed asymmetric transfer hydrogenation with HCOONa as a hydrogen source. A variety of chiral β-hydroxysulfones were obtained in good yields and up to 99.9% ee values. This one-pot process could be easily scaled up for gram-scale synthesis.
- Cui, Peng,Liu, Qixing,Wang, Juan,Liu, Huan,Zhou, Haifeng
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supporting information
p. 634 - 639
(2019/02/14)
-
- Method for synthesizing alpha-sulfone ketone compound from alpha, alpha-dibromo ketone by one-pot process
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The invention discloses a method for synthesizing a high-added-value alpha-sulfone ketone compound from an alpha, alpha-dibromo ketone compound by a one-pot process. The method has the advantages thatan alpha-sulfone ketone derivative is synthesized from alpha, alpha-dibromo ketone, which is simple and easy to obtain, by the one-pot process without separation of an alpha-bromo ketone intermediate, so that a separation process for an intermediate product is omitted, the steps are reduced, and requirements for environment protection are met; the steps of the method are simple and easy to operate, no transition metal reagents are required, and economical sulfonate with less pollution is directly used as a promoter and a sulfonating agent for reducing debromination of the alpha, alpha-dibromoketone, so that the cost is reduced, and economic benefits of reactions are increased; a system for preparing the alpha-sulfone ketone derivative by the one-pot process is developed to provide a novel synthesis method for preparation of the alpha-sulfone ketone compound, and the method has good industrialization prospect and potential application value.
- -
-
Page/Page column 10
(2019/10/17)
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- Visible-light promoted aerobic difunctionalization of alkenes with sulfonyl hydrazides for the synthesis of β-keto/hydroxyl sulfones
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A practical method has been developed for the conversion of alkenes to β-keto/hydroxyl sulfones by their reaction with sulfonyl hydrazides under metal-free conditions. This reaction proceeds through the oxidative addition of alkenes by sulfonyl radicals that are generated by visible-light induced oxidation of sulfonyl hydrazides. Notaly the reaction uses O2 as the terminal oxidant, instead of metal catalysts or oxidants like TBHP, leading to H2O and N2 as the clean by-products. The key features of this reaction include readily available reagents, mild reaction conditions and broad substrate scope.
- Wu, Jie,Zhang, Yulan,Gong, Xinchi,Meng, Yunge,Zhu, Chunyin
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supporting information
p. 3507 - 3513
(2019/04/14)
-
- A metal-free and regioselective approach to (Z)-β-fluorovinyl sulfones and their chemoselective hydrogenation to β-fluoroalkyl sulfones
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A highly regioselective, metal-free hydrofluorination reaction of alkynyl sulfones was developed using TBAF—one of the cheapest and most commonly available fluoride sources. In addition, the reactivity of the resulting β-fluorovinyl sulfones was studied, focusing on their selective hydrogenation reaction. Both β-fluorovinyl sulfones and their hydrogenation products β-fluoroalkyl sulfones may find applications in medicinal and agrochemical sciences.
- Sedgwick, Daniel M.,Román, Raquel,Barrio, Pablo,Morales, Cristina,Fustero, Santos
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p. 108 - 116
(2018/01/01)
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- Metal-free TBAI-catalyzed oxidative Csp3–S bond formation through Csp2–Csp2 bond and S–N bond cleavage: A new route to β-keto-Sulfones
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A novel TBAI-catalyzed radical sulfonylation of readily available N,N-dimethylenaminones with sulfonylhydrazides to afford functionalized β-keto-sulfones has been developed. Various functional groups were tolerated well under the present oxidative conditions and the corresponding β-keto-sulfone compounds were obtained in moderate to good yields. Importantly, this transformation offered the first protocol for Csp3–S bond formation by oxidative Csp2–Csp2 bond cleavage in one step.
- Tang, Yucai,Chen, Ying,Liu, Hui,Guo, Min
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p. 3703 - 3705
(2018/09/14)
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- Efficient sulfonylation of ketones with sodium sulfinates for the synthesis of β-keto sulfones
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The oxidative sulfonylation of ketones with sodium sulfinates as the sulfone source and DMSO as the oxidant is reported. A series of β-keto sulfones were obtained in good to excellent yields. The advantages of this efficient protocol include the low cost of DMSO and HBr, and a broad scope.
- Deng, Siqi,Liang, En,Wu, Yinrong,Tang, Xiaodong
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p. 3955 - 3957
(2018/09/27)
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- Copper Triflate Mediated α-Monohalogenation of α-Diazo β-Ketosulfones with Ammonium Halides
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Copper triflate mediated α-monohalogenation of α-diazo β-ketosulfones with ammonium halides provides the corresponding α-halo β-ketosulfones. Different metal triflates are investigated for this facile and efficient transformation. A plausible mechanism is proposed.
- Chan, Chieh-Kai,Wang, Heui-Sin,Hsu, Ru-Ting,Chang, Meng-Yang
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p. 2045 - 2056
(2017/04/26)
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- Construction of Sulfonyl Oxabenzo[3.3.1]bicyclic Core via Cyclocondensation of β-Ketosulfones and o-Formyl Allylbenzenes
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NH4OAc mediated domino Knoevenagel/Diels-Alder cyclocondensation of β-ketosulfones 1 and o-formyl allylbenzenes 2 provides sulfonyl oxabenzo[3.3.1]bicyclic core 4 in a cosolvent of toluene and HOAc (v/v = 1/1) at reflux for 3 h. The intermediate 3 contains a chalcone motif. The uses of various ammonium salts and solvent systems are investigated for facile and efficient transformation. The plausible mechanisms have been proposed and the DFT calculations have been included.
- Hsueh, Nai-Chen,Chen, Hsing-Yin,Chang, Meng-Yang
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p. 13324 - 13332
(2017/12/26)
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- O -Iodoxybenzoic Acid (IBX)-Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones
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A combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields.
- Katrun, Praewpan,Songsichan, Teerawat,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
-
supporting information
p. 1109 - 1121
(2017/02/24)
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- Synthesis of (E)-1,4-diaryl-2-butene-1,4-diones
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We report a facile route for the preparation of symmetric and unsymmetric (E)-1,4-diaryl-2-butene-1,4-diones 3 by a two-step route, including (1) nucleophilic substitution of 1 with sulfinic acid sodium salts, and (2) K2CO3 mediated alkylation of β-ketosulfones 4 with 1 followed by sequential desulfonylation of the resulting 1,4-diketones 5 in acetone. These products were obtained in high yields.
- Chan, Chieh-Kai,Chang, Meng-Yang
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p. 390 - 405
(2017/01/29)
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- Synthesis of 2-sulfonyl ketone compound by the method
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The invention discloses a method for synthesizing 2-sulfonyl ketone compounds. The method comprises the following steps: mixing substituted N-vinyl acetamide, sulfohydrazide compounds, a catalyst, an oxidant and a solvent to obtain a mixed liquid; and reacting for 2-12 hours at 20-120 DEG C; and then, decompressing to remove the solvent and separating to obtain the 2-sulfonyl ketone compounds, wherein the catalyst is organic amine salt, the oxidant is peroxide and the molar ratio of the sulfohydrazide compound to the substituted N-vinyl acetamide is (1-3):1. The invention provides a new route for synthesizing the 2-sulfonyl ketone compounds. By taking N-vinyl acetamide and the sulfohydrazide compounds as raw materials, the substrate is good in adaptability and corresponding 2-sulfonyl ketone compounds can be synthesized by various substituents. The method is mild in reaction condition, safe and environmental friendly and free from exhaust gases.
- -
-
Paragraph 0084; 0085
(2016/10/08)
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- Visible-light-promoted syntheses of β-keto sulfones from alkynes and sulfonylhydrazides
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A variety of functionalized β-keto sulfones were smoothly prepared through oxysulfonylation of commercially available alkynes with sulfonylhydrazides under the synergistic interactions of visible light irradiation, Ru(bpy)3Cl2 photocatalyst, oxygen, KI, and NaOAc basic additive under very mild reaction conditions.
- Cai, Shunyou,Chen, Danling,Xu, Yaohui,Weng, Wen,Li, Lihuang,Zhang, Ruijie,Huang, Mingqiang
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supporting information
p. 4205 - 4209
(2016/05/24)
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- Aerobic Nickel-Catalyzed Hydroxysulfonylation of Alkenes Using Sodium Sulfinates
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Nickel-catalyzed hydroxysulfonylation of alkenes was achieved using sodium sulfinates under air atmosphere. The procedure enabled the selective synthesis of β-hydroxysulfones in good yields and suppressed the formation of β-ketosulfones. On the contrary, sulfonylation of alkynes with sodium sulfonates afforded only β-ketosulfones.
- Taniguchi, Nobukazu
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p. 7797 - 7802
(2015/08/18)
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- Copper-catalyzed coupling of oxime acetates with sodium sulfinates: An efficient synthesis of sulfone derivatives
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Sulfone derivatives are important synthetic intermediates. However, the general method for their preparation is through traditional coupling reaction: the alkylation of sodium sulfinates with phenacyl halides. Based on our previous work on sodium sulfinates and oxime acetates, we herein report a novel method for sulfone derivatives by oxidative coupling with sodium sulfinates and oxime acetates using copper as catalyst. The sulfonylvinylamine products could be formed in excellent yields. Upon hydrolysis by silica gel in CH 2Cl2, β-ketosulfones could also be efficiently constructed. Various sulfonylvinylamines and β-ketosulfones were obtained in good to excellent yields under the optimized reaction conditions. Mechanistic studies indicated that this transformation involved copper-catalyzed N-O bond cleavage, activation of a vinyl sp2 C-H bond, and C-S bond formation. The oxime acetates act as both a substrate and an oxidant, thus the reaction needs no additional oxidants or additives. Copper brings us together: The title reaction involves copper-catalyzed N-O bond cleavage, activation of a vinyl sp2 C-H bond and C-S bond formation; it uses simple oxime acetates and sodium sulfinates to synthesize sulfonylvinylamine products without the need for additional oxidants or additives. Upon hydrolysis, useful β-ketosulfones are obtained.
- Tang, Xiaodong,Huang, Liangbin,Xu, Yanli,Yang, Jidan,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 4205 - 4208
(2014/05/06)
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- Synthesis of ionic liquid-supported hypervalent iodine reagent and its application as a 'catch and release' reagent for α-substituted acetophenones
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A novel imidazolium-based ionic liquid-supported hypervalent iodine reagent has been synthesized and employed for a 'catch and release' strategy with substituted acetophenones to generate various α-substituted acetophenones in good to excellent yields. The use of an ionic liquid-supported hypervalent iodine reagent avoids chromatographic separation for the purification of α-substituted acetophenones and thus makes the method greener.
- Muthyala, Manoj Kumar,Choudhary, Sunita,Kumar, Anil
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p. 14297 - 14303
(2014/04/17)
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- Chemoselective one-pot synthesis of β-keto sulfones from ketones
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A practical method to synthesize substituted β-keto sulfones directly from ketones at room temperature has been developed. This method involves the nucleophilic addition of a base generated enolate to sulfonyl iodide. The reaction shows high chemoselectivity for the addition of a sulfonyl group to an α-carbon over a hydroxyl group. In addition, the given protocol provides good to excellent yields of β-keto sulfones under mild reaction conditions. Moreover, the regiochemical aspect of the protocol is also explored.
- Rawat, Vikas S.,Reddy, Perla L. M.,Sreedhar, Bojja
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p. 5165 - 5168
(2014/01/23)
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- Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature
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On the basis of the far higher solubility of oxygen gas inside the hydrocarbon core of nanomicelles, metal and peroxide free aerobic oxidation of aryl alkynes to β-ketosulfones has been achieved in water at room temperature. Many examples are offered that illustrate broad functional group tolerance. The overall process is environmentally friendly, documented by the associated low E Factors. It's all happenin' in the micelle! The highly preferential dissolution of oxygen gas within the lipophilic cores inside nanomicelles leads to efficient trapping of in situ generated vinyl radicals. These intermediate radicals, derived from arylalkynes and sulfinic acids, lead to β-ketosulfone products, formed under especially mild and green conditions: no metals, no heating or cooling, recyclable aqueous media, and low E Factors.
- Handa, Sachin,Fennewald, James C.,Lipshutz, Bruce H.
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supporting information
p. 3432 - 3435
(2014/04/03)
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- Synthesis of 2-arylbenzimidazole analogues
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Substituted 2-arylbenzimidazoles (4) were easily synthesized in good yields starting from the condensation reaction of 1,2-diaminobenzenes (1) with β-ketosulfones (5) in the presence of boiling HOAc.
- Chang, Meng-Yang,Chan, Chieh-Kai,Chen, Yi-Chia
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p. 1229 - 1236
(2014/05/20)
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- Sulfonation and trifluoromethylation of enol acetates with sulfonyl chlorides using visible-light photoredox catalysis
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A mild, practical method to prepare α-sulfonyl and α-trifluoromethyl ketones from readily available enol acetates and sulfonyl chlorides has been developed using visible-light photoredox catalysis. The method could be used with a wide range of enol acetates and sulfonyl chlorides, and gave the desired products in satisfactory to excellent yields. A practical method to prepare α-sulfonyl and α-trifluoromethyl ketones from enol acetates and sulfonyl chlorides using visible-light photoredox catalysis is presented. Copyright
- Jiang, Heng,Cheng, Yuanzheng,Zhang, Yan,Yu, Shouyun
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supporting information
p. 5485 - 5492
(2013/09/02)
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- IBX/Imediated reaction of sodium arenesulfinates with alkenes: Facile synthesis of β-keto sulfones
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A direct synthesis of -keto sulfones from alkenes is described. A combination of o-iodoxybenzoic acid/iodine (IBX/I was found to mediate the reactions of alkenes with arenesulfinates to yield -keto sulfones in good yields via a one-pot reaction. Georg Thieme Verlag Stuttgart · New York.
- Samakkanad, Natthapol,Katrun, Praewpan,Techajaroonjit, Thanachart,Hlekhlai, Sornsiri,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
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experimental part
p. 1693 - 1699
(2012/07/03)
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- Silver(I)-mediated reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides: Unexpected formation of vinyl sulfones
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A novel reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides was performed in the presence of silver nitrate or triflate. Conjugated vinyl sulfones as dramatic products were obtained in moderate yields and with Z-selectivity. A free radical mechanism has been proposed to account for the formation of the products.
- Deng, Gui Sheng,Sun, Teng Fei
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p. 1115 - 1118,4
(2020/08/20)
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- A regioselective catalyst- and additive-free synthesis of β-keto sulfones from aryl acetylenes and sodium arenesulfinates
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A facile and regioselective procedure for the preparation of β-keto sulfones has been developed through a simple reaction of aryl acetylenes and sodium arenesulfinates in nitroethane as a solvent at 50°C. The procedure is catalyst- and additive-free and shows a wide range of functional-group tolerance. In this system the formation of new C-O and C-S bonds occurs in a one-pot procedure. Georg Thieme Verlag Stuttgart · New York.
- Sreedhar, Bojja,Rawat, Vikas S.
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supporting information; experimental part
p. 413 - 417
(2012/03/11)
-
- 1-Butyl-3-methylimidazolium p-toluenesulfinate: A novel reagent for synthesis of sulfones and β-ketosulfones in ionic liquid
-
A novel task-specific ionic liquid, 1-butyl-3-methylimidazolium p-toluenesulfinate, [bmim][p-TolSO2] has been synthesized and used as a nucleophile for the reaction with alkyl bromides and phenacyl bromides to prepare sulfones and β-ketosulfones in excellent yields (80-93%) in [bmim][BF4] ionic liquid. The isolated yields of sulfones and β-ketosulfones were higher in [bmim][BF4] than other organic solvents at room temperature.
- Kumar, Anil,Muthyala, Manoj Kumar
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p. 5368 - 5370
(2011/10/31)
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- Synthesis of substituted quinolines using the dianion addition of N-Boc-anilines and α-tolylsulfonyl-α,β-unsaturated ketones
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A short and versatile synthesis of substituted quinolines is provided. Alkylation of sodium tolylsulfinate with bromomethyl- or chloromethyl ketones generates β-keto sulfones. Knoevenagel condensation of the β-keto sulfones with an aldehyde provides α-tolylsulfonyl-α,β-unsaturated ketones. Michael addition of the dianion of N-Boc-anilines in the presence of CuCN and LiCl with the unsaturated ketone generates a 1,4-adduct, which after deprotection of the Boc group and thermal elimination of the tolyl sulfone provides the quinoline.
- Swenson, Rolf E.,Sowin, Thomas J.,Zhang, Henry Q.
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p. 9182 - 9185
(2007/10/03)
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- Reactions of sulfonyl chlorides with silyl enol ethers catalysed by a ruthenium(II) phosphine complex: Convenient synthesis of β-keto sulfones
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The reactions of alkane- and arene-sulfonyl chlorides with silyl enol ethers in the presence of a ruthenium(II) phosphine complex are found to give β-keto sulfones in good to high yields.
- Kamigata, Nobumasa,Udodaira, Kumiko,Shimizu, Toshio
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p. 783 - 786
(2007/10/03)
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- α-Oxosulfones, 3. - Reactions of Acyclic α-Oxosulfones
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The course of reactions of acyclic α-oxosulfones with protic and aprotic nucleophiles is described.A far-reaching analogy to reactions of acyl halides is noticed.
- Schank, Kurt,Werner, Frank
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p. 1477 - 1481
(2007/10/02)
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