- Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process
-
Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.
- Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
-
supporting information
p. 2152 - 2155
(2021/03/06)
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- Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol
-
Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.
- Chen, Yi-Xuan,Wang, Zhu-Jun,Xiao, Jun-An,Chen, Kai,Xiang, Hao-Yue,Yang, Hua
-
supporting information
p. 6558 - 6562
(2021/08/23)
-
- A three-component reaction of arynes, sodium sulfinates, and aldehydes toward 2-sulfonyl benzyl alcohol derivatives
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A novel three-component reaction of arynes, sodium sulfinates, and aldehydes under mild reaction conditions is described. This transformation provides a direct synthetic approach to 2-sulfonyl benzyl alcohol derivatives, which could be rapidly converted to diverse arylsulfur compounds via the transformation of the corresponding hydroxyl groups. Various aryne precursors, sodium arenesulfinates, and aromatic aldehydes can be effectively converted to the desired products in 40-84% yields (29 examples).
- Chen, Qian,Gao, Yang,Hu, Yifan,Huang, Yuanting,Li, Xianwei,Zhao, Xi
-
p. 7066 - 7073
(2021/08/25)
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- Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron
-
The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.
- Qiu, Di,Li, Songyi,Yue, Guanglu,Mao, Jinshan,Xu, Bei,Yuan, Xinyu,Ye, Fei
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supporting information
(2021/11/04)
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- Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates
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This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.
- Cheng, Lan,Guo, Jianbo,Li, Yufei,Liang, Xin,Wang, Qingmin,Xia, Qing,Zhang, Pei,Zhang, Weihua
-
supporting information
p. 8865 - 8870
(2021/11/30)
-
- Copper catalysed oxidative α-sulfonylation of branched aldehydes using the acid enhanced reactivity of manganese(iv) oxide
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The oxidative coupling of secondary aldehydes and sulfinate salts is achieved using copper catalysis to form α-sulfonyl aldehydes. The use of an acidic co-solvent is important to adjust the oxidation potential of MnO2 as an oxidant. A broad range of sulfonylated aldehydes is prepared, and their further functionalisation is demonstrated. A dual ionic/radical pathway mechanism is proposed.
- Higham, Joe I.,Bull, James A.
-
supporting information
p. 4587 - 4590
(2020/05/05)
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- Synthesis of Sulfones via Ru(II)-Catalyzed Sulfination of Boronic Acids
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Ruthenium(II) complexes catalyze the insertion of sulfur dioxide into (het)aryl and alkenyl boronic acids. The transmetalation-sulfination process proceeds with DABSO in the presence of 5 mol % RuCl2(PPh3)3 in methanol at 100 °C. The intermediate sulfinate salt can be quenched with various electrophiles such as alkyl halides, epoxides, Michael acceptors, and λ3-iodanes in moderate to good yields. The reported sulfone synthesis can be performed either as a direct one-pot or one-pot two-step procedure depending on the reactivity of the electrophile.
- Gulbe, Krista,Turks, Mā ris
-
supporting information
p. 5660 - 5669
(2020/05/19)
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- Electrochemical Radical-Radical Cross-Coupling Approach between Sodium Sulfinates and 2 H-Indazoles to 3-Sulfonylated 2 H-Indazoles
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A direct cross-coupling between sodium sulfinates and 2H-indazoles has been developed under electrochemical conditions. The utilization of a graphite anode and platinum cathode in an undivided cell with a constant current of 7 mA allowed the concurrent oxidations of sulfinates and 2H-indazoles to sulfonyl radical and radical cationic 2H-indazoles, facilitating the direct radical-radical coupling strategy to 3-sulfonylated 2H-indazole derivatives. The transition-metal- A nd redox-reagent-free synthetic approach should serve as a valuable synthetic tool to achieve heteroaromatic compounds.
- Kim, Wansoo,Kim, Hun Young,Oh, Kyungsoo
-
supporting information
p. 6319 - 6323
(2020/09/02)
-
- Alkene: Versus alkyne reactivity in unactivated 1,6-enynes: Regio-And chemoselective radical cyclization with chalcogens under metal-And oxidant-free conditions
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Herein, we have developed metal and oxidant-free visible light-promoted alkene vs. alkyne regio-And chemoselective radical cascade cyclization of electronically unbiased 1,6-enynes with chalcogens to synthesize substituted pyrrolidines bearing chalcogens. The reaction generated three new bonds, namely, C-SO2, C-C, and C-Se under extremely mild conditions. Furthermore, we achieved regio-And chemoselective mono-addition of aromatic thiophenols with unactivated 1,6-enynes. The key features of this protocol are broad substrate scope, environment-friendly conditions, operational simplicity, atom economy, and amenability to gram-scale synthesis. The mechanistic studies corroborate that the reaction proceeds via a radical pathway.
- Kudale, Vishal Suresh,Li, Jing,Mutra, Mohana Reddy,Tsai, Wu-Hsun,Wang, Jeh-Jeng
-
supporting information
p. 2288 - 2300
(2020/04/21)
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- Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives
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A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.
- Wang, Fei,Liu, Bo-Xi,Rao, Weidong,Wang, Shun-Yi
-
supporting information
p. 6600 - 6604
(2020/09/02)
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- Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position
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An efficient and convenient protocol for the direct sulfonylation of BODIPY dyes with sodium sulfinates via a radical process is described for the first time. This transformation presented wide substrate scope and high regioselectivity, providing a series of α-sulfonylated BODIPYs. Meaningfully, the sulfonyl group, as a good leaving group, allowed the facile introduction of a variety of functionalities on the BODIPY core. Moreover, a 2,4-dinitrobenzenesulfonyl (DBS) group substituted BODIPY showed dramatically quenched fluorescence via the photoinduced electron transfer (PET) pathway, and was demonstrated as a new fluorescent probe for selective biothiol detection. This journal is
- Lv, Fan,Guo, Xing,Wu, Hao,Li, Heng,Tang, Bing,Yu, Changjiang,Hao, Erhong,Jiao, Lijuan
-
supporting information
p. 15577 - 15580
(2020/12/30)
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- A Facile Synthesis of 3-(Arylthio)imidazo[1,2-a]pyridin-2(3H)-ones from 2-Aminopyridinium Bromides and Sodium Arenesulfinates
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A simple and convenient method has been developed for the synthesis of 3-(arylthio)imidazo[1,2-a]pyridin-2(3H)-ones through a catalyst-free reaction of 2-aminopyridinium bromides with sodium arenesulfinates. A variety of 3-(arylthio)imidazo[1,2-a]pyridin-2(3H)-ones were obtained in moderate to excellent (33–85 %) yields. The developed protocol is operationally simple, exhibits a broad substrate scope with a wide range of functional groups, and is amenable for gram-scale synthesis.
- Kumar, Anil,Rangan, Krishnan,Saroj
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p. 7015 - 7022
(2020/12/01)
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- Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters
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A convenient visible-light photoredox catalysis has been developed for the synthesis of thioesters from two readily available starting materials: acid chlorides and sodium sulfinates. The facile generation of acyl radical species under the visible light photoredox conditions allows the formation of thiyl radical species from sodium sulfinates via multiple single electron transfer reactions, where the final acyl radical-thiyl radical coupling has been accomplished. The direct radical-radical coupling strategy offers a mild and controlled photochemical approach to important synthetic building blocks such as thioesters.
- Bogonda, Ganganna,Patil, DIlip V.,Kim, Hun Young,Oh, Kyungsoo
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supporting information
p. 3774 - 3779
(2019/05/24)
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- Hydrosulfonylation of Unactivated Alkenes by Visible Light Photoredox Catalysis
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The anti-Markovnikov hydrosulfonylation of unactivated alkenes with sodium sulfinates was realized via [Ir(dF(CF3)ppy)2(dtbbpy)]PF6-mediated visible light photoredox catalysis. The presence of an acid such as acetic acid is essential for the reaction to take place. A variety of unactivated alkenes can be transformed into sulfones with good yield and high regioselectivity using this reaction, which is proposed to proceed by a radical mechanism.
- Wang, Juan-Juan,Yu, Wei
-
supporting information
p. 9236 - 9240
(2019/11/19)
-
- An efficient heterogeneous copper fluorapatite (CuFAP)-catalysed oxidative synthesis of diaryl sulfone under mild ligand- and base-free conditions
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A simple, eco-friendly and efficient method for the synthesis of unsymmetrical diaryl sulfones using heterogeneous copper fluorapatite (CuFAP)-catalysed coupling of aryl sulfonic acid and phenyl boronic acid has been developed with good to excellent yields without use of any ligand, base or co-catalyst. Broad substrate scope and gram scale operations are the important features of this method.
- Kamble, Rohit B.,Chavan, Santosh S.,Suryavanshi, Gurunath
-
supporting information
p. 1632 - 1636
(2019/01/21)
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- A Convenient Synthesis of Sulfones via Light Promoted Coupling of Sodium Sulfinates and Aryl Halides
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A convenient and e?cient synthesis of sulfones from sulfinates and aryl halides was developed. The reaction occurred under UV irradiation without transition metal catalyst or photocatalyst. A radical pathway via single-electron transfer (SET) of electron donor-acceptor (EDA) complex was proposed based on UV-vis spectroscopy, radical inhibiting and trapping experiments. (Figure presented.).
- Chen, Lei,Liang, Jie,Chen, Zhen-yu,Chen, Jie,Yan, Ming,Zhang, Xue-jing
-
supporting information
p. 956 - 960
(2019/01/25)
-
- Copper-Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones
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Tertiary propargylic sulfones are of significant importance in organic synthesis and medicinal chemistry, but to date no general asymmetric synthesis approach has been developed. We disclose a versatile copper-catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates that allows the construction of propargylic sulfones featuring elusive quaternary stereocenters. This method provides the first successful example of such an enantioselective propargylic sulfonylation, features high asymmetric induction, wide functional group tolerance, and scalability, and enables attractive product diversification.
- Gómez, José Enrique,Cristòfol, àlex,Kleij, Arjan W.
-
supporting information
p. 3903 - 3907
(2019/02/24)
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- Pd(II)-Catalyzed Direct Sulfonylation of Benzylamines Using Sodium Sulfinates
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A Pd(II)-catalyzed direct sulfonylation of benzylamines with sodium sulfinates using a removable bidentate directing group is illustrated. The transformation is highly regioselective and tolerates wide functional groups. The mechanistic study reveals that radical species are involved in this reaction. This method delivers a direct synthetic strategy to obtain highly functionalized sulfonylated benzylamines.
- Karmakar, Ujjwal,Samanta, Rajarshi
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p. 2850 - 2861
(2019/03/29)
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- Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates
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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.
- Liu, Saiwen,Chen, Ru,Zhang, Jin
-
-
- Diastereoselective Monofluorocyclopropanation Using Fluoromethylsulfonium Salts
-
Diarylfluoromethylsulfonium salts, alternatives to freons or advanced fluorinated building blocks, are bench stable and easy-to-use sources of direct fluoromethylene (:CHF) transfer to alkenes. These salts enabled development of a trans-selective monofluorinated Johnson-Corey-Chaykovsky reaction with vinyl sulfones or vinyl sulfonamides to access synthetically challenging monofluorocyclopropane scaffolds. The described method offers rapid access to monofluorinated cyclopropane building blocks with further functionalization opportunities to deliver more complex synthetic targets diastereoselectively.
- Melngaile, Renate,Sperga, Arturs,Baldridge, Kim K.,Veliks, Janis
-
supporting information
p. 7174 - 7178
(2019/09/12)
-
- Switchable regioselection of C-H thiolation of indoles using different TMS counterions
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A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.
- Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
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p. 11864 - 11867
(2019/10/11)
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- Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates
-
Copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates to construct substituted lactones has been realized. This protocol employs inexpensive CuCl2 as the catalyst, di-tert-butyl peroxide or O2 as the terminal oxidant, and readily available sodium sulfinates as sulfonylation reagents. High functional group tolerance and excellent yields were demonstrated by the efficient preparation of a wide range of γ-sulfonylated phthalides.
- Xiong, Yan-Shi,Zhang, Bin,Yu, Yang,Weng, Jiang,Lu, Gui
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p. 13465 - 13472
(2019/10/16)
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- Convenient method for preparation of aryl sulfinates from arenes and DABSO as the SO2 surrogates
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A safe and efficient protocol for the synthesis of aryl sulfinates from arenes and 1,4-diazabicyclo[2,2,2]octane bis(sulfur dioxide) (DABSO) under mild conditions is described. Through in situ infrared spectroscopic studies, a plausible mechanism for the sulfination reaction is proposed as well.
- Wang, Tianlei,Wang, Fumin,Shen, Jinghua,Pang, Tianting,Ren, Yanfei,Wu, Botao,Zhang, Xubin
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p. 1183 - 1187
(2018/02/26)
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- Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions
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An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
- Liu, Yanan,Xie, Peizhong,Sun, Zuolian,Wo, Xiangyang,Gao, Cuiqing,Fu, Weishan,Loh, Teck-Peng
-
supporting information
p. 5353 - 5356
(2018/09/13)
-
- Design, synthesis and biological evaluation of novel 2-sulfonylindoles as potential anti-inflammatory therapeutic agents for treatment of acute lung injury
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Acute lung injury (ALI) is primarily driven by inflammation that severely impacts lung function. Novel 2-sulfonylindoles were recently shown to exhibit anti-inflammatory activity through the inhibition of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) production. Here, we synthesized 31 compounds which contained 2-sulfonylindole structure. The compounds 8a, 9g, 9h and 9k exhibited dose-dependent anti-inflammatory activity in vitro. Structural-activity relationship analysis revealed that the introduction of sulfonyl group in indole nucleus may be successful to obtain new anti-inflammatory structures and leads. The compounds 9h and 9k also decreased liposaccharide (LPS)-induced IL-6, IL-1β and vascular cell adhesion molecule-1 (VCAM-1) mRNA expression, both in vitro and in an in vivo model of ALI. Furthermore, the compounds 9h and 9k at a high dose (20 mg/kg) significantly protected against LPS-induced ALI in mice. These results show that compounds 9h and 9k could be a promising lead structure for the treatment of ALI.
- Xia, Qinqin,Bao, Xiaodong,Sun, Chuchu,Wu, Di,Rong, Xiaona,Liu, Zhiguo,Gu, Yugui,Zhou, Jianmin,Liang, Guang
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p. 120 - 132
(2018/10/21)
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- A radical cyclization cascade of 2-alkynylbenzonitriles with sodium arylsulfinates
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A convenient radical cyclization cascade procedure for the construction of sulfonated indenones from 2-alkynylbenzonitriles and sodium arylsulfinates has been explored under mild reaction conditions. The present methodology offers a low-cost and operationally straightforward approach to synthesizing various sulfonated indenones in moderate to good yields by simple use of cheap sodium persulfate as an oxidant and environmentally benign water as a co-solvent.
- Zhou, Bang,Chen, Wenqi,Yang, Yuzhong,Yang, Yuan,Deng, Guobo,Liang, Yun
-
supporting information
p. 7959 - 7963
(2018/11/21)
-
- Monofluoromethylthiolation reagent, and preparation method, preparative intermediate and application thereof
-
The invention discloses a monofluoromethylthiolation reagent, and a preparation method, preparative intermediate and application thereof. Structure of the monofluoromethylthiolation reagent is shown as in formula I that is shown in the description, wherein R1, R2, R3, R4 and R5 are respectively chosen from one or any of H, C1-C6 linear or branched alkyl, C1-C6 linear or branched alkoxy, C1-C6 linear or branched halogenated alkyl, halogen, nitryl, hydroxyl, cyano group and amino independently. Monofluoromethylthio group is introduced into molecules directly, so that compared with indirect introduction methods in the prior art, the method for the monofluoromethylthiolation reagent has the advantages of good safety, high efficiency, low cost, high substrate universality, mild condition and wide application range. The monofluoromethylthiolation reagent successfully realizes bifunctional reaction of inactivated olefin, coupling reaction of arylboronic acid and other reactions, and an important methodology research foundation is provided for medicine, pesticide, material and other fields.
- -
-
Paragraph 0192; 0193; 0194
(2017/09/05)
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- Generation of trifluoromethyl thiolsulphonate through one-pot reaction of sulfonyl chloride and trifluoromethanesulfanylamides
-
A novel and efficient tandem reaction of sulfonyl chloride and trifluoromethylsulfanylamide is described here for the synthesis of various trifluoromethyl thiolsulphonates with a broad functional group tolerance. In the process, it is believed that sulfinate generated from sulfonyl chloride is a critical intermediate and the additive 4-methylbenzenesulfonic acid (p-TsOH) facilitates the formation of “CF3S+”. Electrophilic trifluoromethylthiolation of in situ generated sulfinate and “CF3S+” provides the final products.
- Li, Yuewen,Qiu, Guanyinsheng,Wang, Hailong,Sheng, Jie
-
supporting information
p. 690 - 693
(2017/01/28)
-
- Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent
-
A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.
- Wang, Li-Jing,Chen, Manman,Qi, Lin,Xu, Zhidong,Li, Wei
-
supporting information
p. 2056 - 2059
(2017/02/15)
-
- Enantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis
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Detailed herein is the photochemical organocatalytic enantioselective α-alkylation of aldehydes with (phenylsulfonyl)alkyl iodides. The chemistry relies on the direct photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemical control over the radical trapping process. The phenylsulfonyl moiety, acting as a redox auxiliary group, facilitates the generation of radicals. In addition, it can eventually be removed under mild reducing conditions to reveal methyl and benzyl groups.
- Filippini, Giacomo,Silvi, Mattia,Melchiorre, Paolo
-
supporting information
p. 4447 - 4451
(2017/04/13)
-
- Iron-catalyzed synthesis of arylsulfinates through radical coupling reaction
-
A novel strategy for installation of a sulfonyl fragment into arenes has been accomplished via an iron-catalyzed radical coupling reaction. Arene radicals derived from diaryliodoniums via single electron transfer reaction combine with sulfoxylate anion radicals readily generated from commercially available rongalite (HOCH2SO2Na·2H2O) to afford arylsulfinates efficiently at room temperature. In this protocol, a broad range of functional groups are tolerated to give products in good yields.
- Zhang, Weixi,Luo, Meiming
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p. 2980 - 2983
(2016/02/19)
-
- Synthesis of sodium aryl sulfinates from aryl bromides employing 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) as a bench-stable, gas-free alternative to SO2
-
A convenient two-step protocol for the synthesis of sodium aryl sulfinates from aryl bromides and the SO2 surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) has been developed. A wide range of aryl bromides with respect to electronic properties were employed to give the corresponding sodium arylsulfinates in good to excellent yields. The protocol is especially efficient for electron poor aryl bromides which are often difficult to prepare using existing methods.
- Skillinghaug, Bobo,Rydfjord, Jonas,Odell, Luke R.
-
supporting information
p. 533 - 536
(2016/01/20)
-
- Method for preparing aryl sulfinate
-
The invention provides a method for preparing an aryl sulfinate compound through the reaction of diaryl iodonium salt and sodium formaldehyde sulfoxylate.At room temperature, the diaryl iodonium salt reacts with the sodium formaldehyde sulfoxylate for 10-120 minutes to generate the corresponding aryl sulfinate compound.The method has the advantages that the reaction conditions are mild, the used reagents re easy to obtain, the application range of a substrate is wide, operation is simple, reaction is quick, and the like.
- -
-
Paragraph 0016
(2016/10/08)
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- Synthesis of Substituted Pyrroles via Copper-Catalyzed Cyclization of Ethyl Allenoates with Activated Isocyanides
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A new method for the synthesis of di- and trisubstituted pyrroles via copper-catalyzed cyclization of ethyl allenoates with activated isocyanides has been developed. In contrast to related annulation reactions previously reported, this new process features a skeletal rearrangement in which the aryl sulfonyl moiety, which functions as the electron-withdrawing group in the α-carbon of the isocyanide, was found to migrate to the γ-carbon of the starting allenoate in the final product for the first time.
- Lu, Kui,Ding, Fang,Qin, Long,Jia, Xiaoliang,Xu, Chuanming,Zhao, Xia,Yao, Qingwei,Yu, Peng
-
supporting information
p. 2121 - 2125
(2016/08/12)
-
- Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate
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An unexpected Cu-catalyzed deoxygenative C2-sulfonylation reaction of quinoline N-oxides in the presence of radical initiator K2S2O8 was developed that used sodium sulfinate as a sulfonyl coupling partner. The mechanism studies indicate that the reaction proceeds via Minisci-like radical coupling step to give sulfonylated quinoline with good chemical yields.
- Du, Bingnan,Qian, Ping,Wang, Yang,Mei, Haibo,Han, Jianlin,Pan, Yi
-
supporting information
p. 4144 - 4147
(2016/08/30)
-
- Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature
-
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
-
supporting information
p. 1395 - 1399
(2015/03/18)
-
- Copper-mediated ortho C-H sulfonylation of benzoic acid derivatives with sodium sulfinates
-
Copper-mediated direct ortho C-H bond sulfonylation of benzoic acid derivatives with sodium sulfinates was achieved by employing an 8-aminoquinoline moiety as the bidentate directing group. Various aryl sulfones were synthesized in good yields with excellent regioselectivity. This journal is
- Liu, Jidan,Yu, Lin,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Wang, Wenduo,Tan, Ze
-
supporting information
p. 6418 - 6421
(2015/04/14)
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- Visible Light-Mediated Metal-Free Synthesis of Vinyl Sulfones from Aryl Sulfinates
-
Visible light and eosin Y catalyze the synthesis of vinyl sulfones from aryl sulfinates and alkenes by a photoredox process. The reaction scope is broad in aryl sulfinates and alkenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable vinyl sulfones.
- Meyer, Andreas Uwe,J?ger, Stefanie,Prasad Hari, Durga,K?nig, Burkhard
-
supporting information
p. 2050 - 2054
(2015/06/23)
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- Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides
-
Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright
- Liu, Jidan,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Yang, Zhiyong,Tan, Ze
-
supporting information
p. 3196 - 3202
(2014/06/09)
-
- Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies
-
A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).
- Skillinghaug, Bobo,Sk?ld, Christian,Rydfjord, Jonas,Svensson, Fredrik,Behrends, Malte,S?vmarker, Jonas,Sj?berg, Per J. R.,Larhed, Mats
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p. 12018 - 12032
(2015/01/16)
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- Copper-catalysed coupling of aryl tosylates with sodium arylsulfinates
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Diaryl sulfones derivatives were easily synthesised from aryl tosylates and sodium arylsulfinates in high yields using [Cu(CH3CN)4]PF6 as catalyst. The transformation is efficient, simple and the starting materials are readily available.
- Wang, Chunjie,Zhang, Hui,Li, Zhiwei,Wang, Ziyun
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p. 639 - 642
(2015/02/02)
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- First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates
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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.
- Tian, Heng,Cao, Aijuan,Qiao, Lijun,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
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supporting information
p. 9107 - 9112
(2015/03/05)
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- Synthesis and promising in Vitro antiproliferative activity of sulfones of a 5-nitrothiazole series
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The synthesis in water of new sulfone derivatives under microwave irradiation is described. This eco-friendly process leads to the expected products in good yields by reaction of various substituted sulfinates (commercially available or obtained by reduction of the corresponding sulfonyl chlorides) with 4-chloromethyl-2-methyl-5-nitro-1,3- thiazole. In order to evaluate the antiproliferative effect of these compounds, several sulfone derivatives are also dichlorinated on the Ca next to the sulfonyl group. An evaluation on different cancer cell lines reveals promising selective in vitro antiproliferative activity toward HepG2 human cell lines by dihydrogenated sulfones, suggesting further research should be to explore their anticancer potential in the treatment of liver cancer.
- Cohen, Anita,Crozet, Maxime D.,Rathelot, Pascal,Azas, Nadine,Vanelle, Patrice
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- BENZOFURO[3,2-c] PYRIDINES AND RELATED ANALOGS AS SEROTONIN SUB-TYPE 6 (5-HT6) MODULATORS FOR THE TREATMENT OF OBESITY, METABOLIC SYNDROME, COGNITION AND SCHIZOPHRENIA
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The present invention relates to benzofuro[3,2-c]pyridine and azepine analogs as serotonin sub-type 6 (5-HT6) modulators, pharmaceutical compositions including these compounds, methods of preparation, and use thereof. These compounds are useful in the treatment of central nervous system disorders including obesity, metabolic syndrome, cognition, schizophrenia, attention deficit hyperactivity disorder, bipolar disorder, rare and orphan diseases, and sleep disorders. The subject compounds have the structure of formula (I) with the substituents being described herein.
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Page/Page column 33-34
(2012/07/28)
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- Palladium-catalyzed desulfitative addition of sodium sulfinates with α,β-unsaturated carbonyl compounds
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A palladium-catalyzed desulfitative conjugate addition of sodium sulfinates with α,β-unsaturated carbonyl compounds is described. The reaction showed very good selectivity and tolerated a wide range of functionalities under an atmosphere of argon.
- Chen, Wen,Zhou, Xianya,Xiao, Fuhong,Luo, Jiaying,Deng, Guo-Jun
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supporting information; experimental part
p. 4347 - 4350
(2012/09/25)
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- EPIMINOCYCLOALKYL(B)INDOLE DERIVATIVES AS SEROTONIN SUB-TYPE 6 (5-HT6) MODULATORS AND USES THEREOF
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The present invention relates to epiminocycloalkyl[b]indole derivatives as serotonin sub-type 6 (5-HT6) modulators, pharmaceutical compositions including these compounds, and methods of preparation and use thereof. These compounds are useful in the treatment of central nervous system disorders including obesity, metabolic syndrome, cognition, and schizophrenia. The subject compounds have the structure of formula (I), with the substituents being described herein.
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Page/Page column 40
(2011/04/26)
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- Rapid synthesis of sulfone derivatives as potential anti-infectious agents
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An original one-pot microwave reaction was developed for the synthesis of sulfone derivatives as new potent antimicrobial agents. This eco-friendly methodology conducted in 30 min led to desired products with good yields. The sulfones (4a and 4b) were obtained via the reaction of 3a with the corresponding halo-derivatives in the presence of sodium hydride. All compounds were tested for their antibacterial and antifungal activities against four bacterial strains (two gram positive, and two gram negative ones) and two yeasts. The disk diffusion method has shown an interesting antibacterial activity for seven compounds (3b-g and 4b) against Staphylococcus aureus. Among these seven compounds, five derivatives (3b-e and 3g) showed activity against Candida tropicalis.
- Curti,Laget,Carle, A. Ortiz,Gellis,Vanelle
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p. 880 - 884
(2008/02/12)
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- PROCESS FOR PREPARATION OF AROMATIC DISULFIDE
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Provides is a process for preparing aromatic disulfide using aromatic sulfonyl chloride as a starting material and via aromatic sulfonate as an intermediate. The process of the present invention secures industrially advantageous reaction conditions via use of an iodine derivative as a catalyst, is economically advantageous due to use of inexpensive starting materials and reducing agents as compared to known methods and recovery of the catalyst, and can maximize the purity of the products via re-oxidation of thiophenol which is present as impurities in aromatic disulfide that is a final product of reduction reaction. The present invention can be widely applied to various fields of fine chemistry.
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Page/Page column 13-14
(2008/06/13)
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- &β-(N,N-Dialkylamino)ethyl Arylthiosulfonates: New Simulants for O-Ethyl S- Methylphosphonothioate
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β-(N,N-Dialkylamino)ethyl arylthiosulfonates 2, new simulants for the hydrolysis and oxidation chemistry of VX (1), are prepared in good yield by reaction of a potassium arylthiosulfonate with a 2-chloroethylamine.Alkaline hydrolysis of 2 results in cleavage of the S-S-bond to give sulfinic acids and disulfides.Like VX, oxidation of 2 by N-sulfonyloxaziridine 12 occurs exclusively on nitrogen to give the corresponding amine oxide which subsequently undergoes a Cope elimination reaction affording the vinyl sulfide 14.
- Davis, Franklin A.,Ray, Jayanta K.,Kasperowicz, Steve,Przeslawski, Robert M.,Durst, H. Dupont
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p. 2594 - 2599
(2007/10/02)
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