- Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: Access to functionalized coumarins or quinolinones
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A direct electrochemical oxidative cyclization of alkynoates and alkynamides with diselenides or disulfides for the synthesis of coumarins and quinolinones bearing a chalcogen functional group has been developed. This green and efficient approach was realized through a constant current electrolysis in an undivided cell under metal-free and oxidant-free conditions. Moreover, a series of selenium/sulfur-substituted coumarin and quinolinone products were obtained in moderate to good yields with a broad scope and functional group tolerance.
- Hua, Jiawei,Fang, Zheng,Xu, Jia,Bian, Mixue,Liu, ChengKou,He, Wei,Zhu, Ning,Yang, Zhao,Guo, Kai
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- Formation of diphenyl sulfoxide and diphenyl sulfide via the aluminum chloride-facilitated electrophilic aromatic substitution of benzene with thionyl chloride, and a novel reduction of sulfur (IV) to sulfur (II)
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The aluminum chloride (AlCl3)-facilitated electrophilic aromatic substitution (EAS) reaction of benzene (PhH) with thionyl chloride (SOCl 2) in the molar ratio of PhH:SOCl2:AlCl3 = 2:1:1 was studied under different conditions. At about 70C, adding granular AlCl3 (equimolar to SOCl2) piecewise to a 2:1 mixture of PhH and SOCl2 led to formation of a highly pure (99.9%) sole product of diphenyl sulfoxide (Ph2SO) in an isolated yield of 85% after aqueous workup. It represents a simple and very efficient synthesis of Ph 2SO, an important fundamental organic reagent. At about 0C, adding PhH (twice the molar quantity of SOCl2) to a 1:1 mixture of SOCl 2 and AlCl3 gave both diphenyl sulfide Ph2S (yield: 37%) and Ph2SO (yield: 27%) after aqueous workup, together with a small amount of S-phenyl benzenesulfonothioate PhSO2SPh (yield: about 5%) and a trace amount of diphenyl sulfone (Ph2SO 2). A possible mechanism has been proposed to account for formation of all these products, especially for the formation of Ph2S [S (II)] from SOCl2 [S (IV)], which involves a novel reduction of sulfur in the course of the EAS reaction. Taylor & Francis Group, LLC.
- Sun, Xiaoping,Haas, David,Sayre, Kayanna,Weller, Donald
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- A Facile Diastereoselective Synthesis of Functionalized 1,2,3-Trisubstituted Benzocyclopentenes through the Cycloaddition of Bis(phenylsulfonyl)iodonium Ylides to Cyclic Alkenes
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The thermal cycloaddition of β-disulfonyl iodonium ylides to cyclic alkenes affords exclusively 1,2,3-trisubstituted cis(1,2)/cis(2,3)-configured benzocyclopentenes by an electrophilic attack of the ylide on the olefinic double bond. This unsual transformation provides a convenient and direct method for the diastereoselective synthesis of functionalized bicyclo [3.3.0] octanes (characteristic structural units contained in polyquinane natural products), when cyclopentenes are used as cycloalkene partner.
- Adam, Waldemar,Gogonas, Efstathios P.,Hadjiarapoglou, Lazaros P.
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- Alkenyl alane-pyridine complexes in a new synthesis of?aryl?alk-1-enyl sulfoxides
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A new and an efficient synthesis of aryl alk-1-enyl sulfoxides is reported. The reaction between alane-pyridine complexes, triphenylphosphine, and sulfonyl chlorides affords the title products in good to excellent yields (70-94%) in short reaction times using mild conditions. The optimal ratio between reagents (alane-pyridine/PPh3/sulfonyl chloride 1.00/1.35/0.92) was obtained performing a chemiometric analysis. A rationale for the reaction was advanced.
- Signore,Calderisi,Malanga,Menicagli
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- NIS-promoted three-component reaction of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides
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A new three-component reaction of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides has been established, and an expanded inventory of 3-aryl-4-(arylthio)-1H-pyrazol-5-amines is synthesized by sequential cyclization and sulfenylation reactions under the action of NIS. In addition to the attractive features of multicomponent reactions, the protocol presents broad substrate scope, good functional group tolerance and mild reaction conditions. The utility of this procedure is further established by gram-scale synthesis as well as the diversified transformations of the products to useful compounds. This journal is
- Wei, Yueting,Liu, Ping,Liu, Yali,He, Jing,Li, Xuezhen,Li, Shiwu,Zhao, Jixing
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- Oxidation of organic sulfides and disulfides with a tert-butyl hydroperoxide-aluminum tri-tert-butoxide system
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Methyl phenylethynyl and phenyl phenylethynyl sulfides are selectively converted into methyl phenylethynyl and phenyl phenylethynyl sulfones, respectively, under the action of system tert-butyl hydroperoxide-aluminum tri-tert-butoxide in benzene at 20 °C. The analogous oxidation of diphenyl disulfide results in S-phenyl benzenethiosulfonate.
- Zaburdaeva,Dodonov
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- Copper(I) Bromide-Dimethyl Sulfide-Catalyzed Direct Sulfanylation of 4-Hydroxycoumarins and 4-Hydroxyquinolinones with Arylsulfonylhydrazides and Selective Fluorescence Switch- On Sensing of Cadmium(II) Ion in Water
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An efficient protocol for the direct sulfanylation of various 4-hydroxycoumarins and 4-hydroxyquinolinones in good yield with arylsulfonylhydrazides as sulfanylating agents was developed via copper(I) bromide?dimethyl sulfide-catalyzed S–O, S–N bond cleavage and C–S cross-coupling reactions. A highly selective fluorescence turning-on sensing of cadmium(II) ions in water using the synthesized 3-sulfanyl-4-hydroxycoumarin derivative was also investigated. (Figure presented.).
- Paul, Sanjay,Shrestha, Rajeev,Edison,Lee, Yong Rok,Kim, Sung Hong
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- Experimental and Computational Evidence for the Formation of Iminopersulfinic Acids
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An experimental and computational study of the reactions of singlet oxygen with N-substituted sulfenamides is reported. Intermediates capable of epoxidizing norbornene were observed during the photooxidations of three sulfenamides. These results are used to argue for formation of iminopersulfinic acids. The structural integrity of two iminopersulfinic acids was supported by their successful location at the MP2/6-31G* level of theory. Furthermore, the inability to locate computationally significant persulfinimide precursors suggests that the iminopersulfinic acids form by enelike reactions involving near-simultaneous addition of singlet oxygen to sulfur and hydrogen abstraction.
- Clennan, Edward L.,Chen, Ming-Fang,Greer, Alexander,Jensen, Frank
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- Metal-free oxidation of sulfides by carbon nitride with visible light illumination at room temperature
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Mesoporous graphitic carbon nitride (mpg-C3N4) has been developed as a non-metal, heterogeneous photocatalyst for the selective oxidation of sulfides to sulfoxides with O2 at room temperature. Especially, the combination of mpg-C3N4 and aldehydes was a highly active system under visible-light irradiation. For example, mpg-C 3N4/isobutyraldehyde catalytic oxidation of methyl phenyl sulfide afforded 97% conversion with 98% selectivity for the methyl phenyl sulfoxide in 4 h. Moreover, the mpg-C3N4 can be easily recovered by filtration and then reused at least four times without losing activity. By exploring the electron spin resonance and some comparative experiments, a catalytic mechanism of this oxidation was provided. Finally, the system also works well in the oxidation of a number of sulfides, including sulfides bearing various groups, and phenyl disulfide. The use of a metal-free heterogeneous catalyst and visible light energy, along with the mild reaction conditions makes this oxidation reaction an environmentally benign and energy-saving chemical process. The Royal Society of Chemistry 2012.
- Zhang, Pengfei,Wang, Yong,Li, Haoran,Antonietti, Markus
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- In Situ Generated HypoIodite Activator for the C2 Sulfonylation of Heteroaromatic N-oxides
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A mild approach for direct C2 sulfonylation of heteroaromatic N-oxides with sulfonyl hydrazides affording 2-sulfonyl quinolines/pyridines has been developed. A variety of heteroaromatic N-oxides and sulfonyl hydrazides participate effectively in this transformation which uses hypoiodites (generated in situ from NaI and TBHP) as a means of substrate activators. In this reaction, the N-oxide plays a dual role, acting as a traceless directing group as well as a source of oxygen atom.
- Su, Yuan,Zhou, Xuejun,He, Chunlian,Zhang, Wei,Ling, Xiao,Xiao, Xia
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- Scalable Synthesis of S-Fluoromethyl Benzenesulfonothioate
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A general and practical method for the preparation of S-fluoromethyl benzenesulfonothioate on a 500 g scale in two steps from readily available CH2FCl, sulfur, and sodium benzenesulfinate is reported. The reaction was found to be rather sensitive to water and temperature. Furthermore, the main side product of the reaction was identified to be S-phenyl benzenesulfonothioate.
- Chen, Wenbo,Lu, Long,Shen, Qilong,Yao, Ruichao,Zhao, Qunchao
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- Photophysics and Photochemistry of Diphenyl Sulfone. 2. Investigation of the S1 Decay Pathways
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An extensive analysis of the S1 deactivation pathways of diphenyl sulfone (DPS) in alcohols and some other solvents is presented.The combined results of steady-state photolysis, time-resolved fluorescence, and steady-state fluorescence measurements at variable temperature and of S1 -> T1 intersystem crossing quantum yield determinations enable a complete characterization of the S1 photophysics and photochemistry of DPS to be obtained.The main S1 decay channel appears to be an activated S1 -> Tn intersystem crossing (Ea ca. 2 kcal/mol), other than S1 -> T1.Although the fluorescence emission and S1 -> T1 quantum yields show some solvent dependence, they play minor roles in the solvents studied.The state eventually reached in the S1 -> Tn activated intersystem crossing is proposed to be a dissociative 3??* state localized on a C-S bond, on the basis of experimental evidence and of some preliminary theoretical data.A simple rationalization of the observations is provided by a model potential energy diagram obtained as an extension of the one previously proposed to account for the results concerning the T1 decay of the same molecule.Two hypotheses on the mechanisms of the above-mentioned S1 -> Tn activated intersystem crossing are put forward and briefly discussed.
- Bruni, Maria Cristina,Ponterini, Glauco,Scoponi, Marco
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- Chemichal Ionization and Electron Impact Mass Spectra of Thiosulfinates, Thiosulfonates, and Sulfinyl Sulfones
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The chemical ionization and electron impact mass spectra of some thiosulfinates, thiosulfonates, and sulfinyl sulfones have been studied.The electron impact mass spectra of four of the six thiosulfonates show molecular ions of less than 1percent.Inconclusive evidence was obtained for sulfenyl sulfinate type intermediates in the electron impact spectra of thiosulfonates.The electron impact spectra of thiosulfonates were similar to those of thiosulfonates.The chemical ionization (isobutane) mass spectra of thiosulfinates and thiosulfonatesgenerally show protonated molecular ions (+) as base peaks and (+) and (+) peaks.
- Freeman, Fillmore,Angeletakis, Christos N.
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- Easy and green synthesis of 6-(arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones in aqueous potassium hydroxide
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A convenient green procedure have been proposed for the synthesis of 6-(2-arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones by condensation of 6-(arylvinyl)-4-hydroxy-2H-pyran-2-ones with S-phenyl benzenesulfonothioate in aqueous potassium hydroxide at room temperature.
- Benferrah,Hammadi,Berthiol
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- A new synthesis of thioesters and selenoesters of triflic acid under oxidative conditions
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Trifluoromethanethio-(or seleno-)sulfonates (CF3SO2YR, Y=S, Se) are easily obtained in one step at 0-20 °C from disulfides (or diselenides), sodium trifluoromethanesulfinate and [bis-(trifluoroacetoxy)iodo]benzene (BTIB).
- Billard, Thierry,Langlois, Bernard R.
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- Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions
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Direct conversion of sulfinamides to thiosulfonates is described. Without the use of additional redox agents, the reaction proceeds smoothly in the presence of TFA under metal-free conditions. This protocol possesses many advantages such as odourless and stable starting materials, broad substrate scope, selective synthesis, and mild reaction conditions. This journal is
- Ji, Yuan-Zhao,Li, Hui-Jing,Wang, Jun-Hu,Wu, Yan-Chao,Zhang, Chi
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p. 9291 - 9298
(2021/11/13)
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- Synthesis of Symmetrical and Unsymmetrical Thiosulfonates from Disulfides through Electrochemically Induced Disulfide Bond Metathesis and Site-Selective Oxidation
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The anodic generation of symmetrical and unsymmetrical thiosulfonates is presented. First, the oxidation of disulfides yielding symmetrical thiosulfonates was realized. The direct synthesis is performed using a simple quasi-divided cell design, whereby using a supporting electrolyte is unnecessary. Its principle was then expanded to the conversion of unsymmetrical disulfides that were generated in situ through metathesis of two symmetrical disulfides. This enables a direct access to unsymmetrical thiosulfonates without any pre-functionalization or elaborate synthesis of the starting materials for the first time. The reaction scope was investigated by converting differently functionalized aliphatic and aromatic disulfides in moderate to very good yields. Furthermore, a sensitivity assessment for an improved reproducibility and a robustness screen to determine the compatibility of the reaction against functional groups were performed.
- Hilt, Gerhard,Strehl, Julia
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supporting information
(2021/10/14)
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- Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution
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The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.
- Liu, En-Chih,Topczewski, Joseph J.
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supporting information
p. 5308 - 5313
(2021/05/04)
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- Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes
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An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.
- Kumari, Arram Haritha,Kumar, Jangam Jagadesh,Krishna, Gamidi Rama,Reddy, Raju Jannapu
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supporting information
p. 2850 - 2864
(2021/05/18)
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- Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-a]benzimidazoles
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A visible-light-induced radical domino reaction of 1-allyl-2-ethynylbenzoimidazoles with thiosulfonates was developed, which generated the thiosulfonylated pyrrolo[1,2-a]benzimidazoles in moderate to good yields. This reaction proceeded under transition-metal-free conditions with good functional group tolerance and high regioselectivity. The possible pathway involved thiosulfonates were activated through the energy transfer route promoted by photocatalysis.
- Liu, Yan,Zhang, Niuniu,Xu, Yanli,Chen, Yanyan
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p. 16882 - 16891
(2021/11/18)
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- Temperature-Controlled Chemoselective Synthesis of Thiosulfonates and Thiocyanates: Novel Reactivity of KXCN (X=S, Se) towards Organosulfonyl Chlorides
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An efficient chemoselective protocol has been developed for the synthesis of thiosulfonates and thiocyanates by employing cost effective and commercially available organosulfonyl chlorides with potassium thio-/selenocyanate. The strategy offered the thiosulfonates and thiocyanates selectively by tuning the equivalents of KSeCN and optimizing the reaction temperature. On the other hand, thiosulfonates were obtained as sole products when organosulfonyl chlorides were treated with KSCN. Furthermore, the syntheses of diarylthioethers and aryl(heteroaryl) thioethers were carried out as a part of synthetic application of newly prepared arylthiocyanates.
- Kalaramna, Pratibha,Goswami, Avijit
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supporting information
p. 5359 - 5366
(2021/10/25)
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- Synthesis of Symmetrical Thiosulfonates via Cu(OTf)2-Catalyzed Reductive Homocoupling of Arenesulfonyl Chlorides
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A variety of symmetrical thiosulfonates are synthesized via Cu-catalyzed reductive homocoupling of aryl sulfonyl chlorides. This protocol uses organic amine acting as a mild reductant and low-cost copper as an effective catalyst. Such a reductive coupling process features a broad substrate scope and good functional group tolerance. Related thiosulfonate products can also be converted into diverse functional molecules.
- Liu, Lixia,Luo, Bo,Wang, Chengming
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supporting information
p. 5880 - 5883
(2021/11/27)
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- Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides
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A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.
- Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Wang, Huimin,Ding, Chengrong
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- Synthesis of symmetrical / unsymmetrical thiosulfonates through the disproportionate coupling reaction of sulfonyl hydrazide mediated by phosphomolybdic acid
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Phosphomolybdic acid (H3PMo12O40) is reported as a green low-cost catalyst for the synthesis of symmetrical / unsymmetrical thiosulfonates via the disproportionate coupling reaction of sulfonyl hydrazide. The attributes of this reported catalytic system include low catalyst loadings (1 mol%), efficient turnover, and high yields (up to 94%). Additionally, this reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via sulfinyl radical disproportionation.
- Lv, Mengting,Liu, Yufeng,Li, Ke,Yang, Guoping
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- The organocatalytic synthesis of perfluorophenylsulfides: Via the thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates
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The organic superbase t-Bu-P4-catalyzed direct thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates was developed. Yields of perfluorophenylsulfides of up to 97% under catalysis of 5 mol% t-Bu-P4 were achieved. This method was shown to provide an efficient way to construct the perfluorophenyl-sulfur bond under mild metal-free reaction conditions. This journal is
- Cai, Zhihua,Du, Guangfen,He, Lin,Lin, Muze,Luo, Jinyun,Wu, Leifang
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supporting information
p. 9237 - 9241
(2021/11/13)
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- Synthesis of (E)-iodo vinylsulfones via oxidative addition of thiol into alkyne under metal free condition
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An efficient, transition-metal free and molecular iodine promoted protocol for the construction of (E)-β-iodovinyl sulfone derivatives via oxidative C–S coupling of thiol and alkyne has been demonstrated. Both aryl and alkyl terminal acetylenes were found to be an excellent substrate for the present reaction which provides a wide range of β-iodovinyl sulfone derivatives with very good yield and excellent regio and stereo-selectivities. Diaryldisulfide is also found to be an equally efficient sulfonyl group surrogate under identical reaction conditions.
- Samanta, Surya Kanta,Sarkar, Rumpa,Bera, Mrinal K.
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supporting information
(2021/07/12)
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- Visible-Light-Induced Cyclization/Aromatization of 2-Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives
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A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed and provided unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the thiosulfonylation product of 2-vinyloxy arylalkyne was the key intermediate, and the additive disulfide played the role of hydrogen abstraction in the aromatization process to offer the desired product. This reaction presents a new reaction mode for the construction of polycyclic oxygen heterocycles.
- Chen, Hui,Chen, Yanyan,Mo, Zuyu,Xu, Yanli,Yan, Yunyun,Zhang, Niuniu
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supporting information
p. 376 - 381
(2021/01/13)
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- Visible-light-promoted synthesis of secondary and tertiary thiocarbamates from thiosulfonates andN-substituted formamides
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A general visible-light-promoted metal-free synthesis of secondary and tertiary thiocarbamates starting from thiosulfonates andN-substituted formamides is developed. By employing rhodamine B as a photocatalyst andtert-butyl hydroperoxide (TBHP) as an oxidant, a wide scope of thiocarbamates can be obtained through direct thiolation of acyl C-H bonds under irradiation of blue light at room temperature for 12 h.
- Bi, Wen-Zhu,Zhang, Wen-Jie,Li, Zi-Jie,He, Yuan-Hao,Feng, Su-Xiang,Geng, Yang,Chen, Xiao-Lan,Qu, Ling-Bo
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supporting information
p. 8701 - 8705
(2021/10/22)
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- Unusual Application for Phosphonium Salts and Phosphoranes: Synthesis of Chalcogenides
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A novel strategy for the synthesis of sulfides and selenides from phosphonium salts and thio- or selenesulfonates, commercially available compounds, is described. When phosphoranes were used in the reaction, different products were obtained. The methodology does not require the use of metals, reactive species, or anhydrous conditions to be performed.
- Moura, Igor M. R.,Tranquilino, Arisson,Sátiro, Barbara G.,Silva, Ricardo O.,De Oliveira-Silva, Diogo,Oliveira, Roberta A.,Menezes, Paulo H.
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p. 5954 - 5964
(2021/05/04)
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- Metal-Free Radical Annulation of Oxygen-Containing 1,7-Enynes: Configuration-Selective Synthesis of (E)-3-((Arylsulfonyl)methyl)-4-Substituted Arylidenechromene Derivatives
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A novel strategy for the synthesis of (E)-3-((arylsulfonyl)methyl)-4-substituted benzylidenechromene derivatives via a metal-free radical annulation reaction of oxygen-containing 1,7-enynes with thiosulfonates has been developed. The reaction shows broad substrate scope, wide functional group tolerance, and moderate to excellent yields. Moreover, thiosulfonates were well driven to achieve the bifunctionalization reaction of oxo-1,7-enynes which derived from aliphatic alkynes. In addition, the (E)-configuration of the products was highly controlled by the structure of 1,7-enyne.
- Bian, Mouwang,Dai, Lei,Mao, Kaimin,Rong, Liangce,Wang, Chang,Yu, Qiuyu,Zhang, Jinghang
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supporting information
p. 218 - 224
(2021/01/13)
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- Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols
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A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.
- Ma, Jinfeng,Xu, Pan,Zhong, Zijian,Zhou, Aihua
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- Competition Between Cα-S and Cα-Cβ Bond Cleavage in β-Hydroxysulfoxides Cation Radicals Generated by Photoinduced Electron Transfer?
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A kinetic and product study of the 3-cyano-N-methyl-quinolinium photoinduced monoelectronic oxidation of a series of β-hydroxysulfoxides has been carried out to investigate the competition between Cα-S and Cα-Cβ bond cleavage within the corresponding cation radicals. Laser flash photolysis experiments unequivocally established the formation of sulfoxide cation radicals showing their absorption band (λmax ≈ 520?nm) and that of 3-CN-NMQ? (λmax ≈ 390?nm). Steady-state photolysis experiments suggest that, in contrast to what previously observed for alkyl phenyl sulfoxide cation radicals that exclusively undergo Cα-S bond cleavage, the presence of a β-hydroxy group makes, in some cases, the Cα-Cβ scission competitive. The factors governing this competition seem to depend on the relative stability of the fragments formed from the two bond scissions. Substitution of the β-OH group with -OMe did not dramatically change the reactivity pattern of the cation radicals thus suggesting that the observed favorable effect of the hydroxy group on the Cα-Cβ bond cleavage mainly resides on its capability to stabilize the carbocation formed upon this scission.
- Lapi, Andrea,D'Alfonso, Claudio,Del Giacco, Tiziana,Lanzalunga, Osvaldo
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p. 1310 - 1321
(2021/06/07)
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- H4SiW12O40-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3,4-disubstituted 1H-pyrazoles
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A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H4SiW12O40)-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides/aldehydes were smoothly reacted with sulfonyl hydrazides to furnish regioselectivity 3,4-disubstituted 1H-pyrazoles. The application of such an earth-abundant, readily accessible, and nontoxic catalyst provides a green approach for the construction of 3,4-disubstituted 1H-pyrazoles. A plausible reaction mechanism has been proposed on the basis of control experiments, GC-MS and DFT calculations.
- Cheng, Mengyuan,Cheng, Yuanyuan,Gao, Xiaofei,Li, Ke,Lin, Xiaoling,Liu, Yufeng,Xie, Xuanjie,Yang, Guoping
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supporting information
(2021/09/06)
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- A Selectfluor-promoted oxidative reaction of disulfides and amines: access to sulfinamides
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An unprecedented transition-metal-free oxidative reaction of disulfides and amines with Selectfluor as a mild oxidant under aerobic conditions was developed. This reaction was conducted under mild conditions and tolerated a wide range of coupling partners including disulfides and amines, affording the corresponding sulfinamide products in good chemical yields. Furthermore, this reaction could be used in gram-scale synthesis. This reaction enriches the research content of Selectfluor and provides a valuable vista for the convenient synthesis of sulfinamides.
- Han, Jianlin,Liu, Jiang,Mei, Haibo,Pajkert, Romana,R?schenthaler, Gerd-Volker
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supporting information
p. 3761 - 3766
(2020/06/03)
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- CuCl2-promoted decomposition of sulfonyl hydrazides for the synthesis of thiosulfonates
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Sulfonyl hydrazides recently received much attention as reagents for the introduction of sulfur-containing functional groups into organic compounds, because both sulfonyl and sulfenyl sources could be generated by the oxidation and decomposition of the sulfonyl hydrazides, respectively. However, the transformations of sulfonyl hydrazides into thiosulfonates, which could be produced by the reaction between sulfonyl and sulfenyl sources, have been less investigated. In this manuscript, we describe CuCl2-promoted selective synthesis of thiosulfonates from sulfonyl hydrazides. A variety of thiosulfonates were produced in moderate to good yields. The mechanism involving radical intermediates such as sulfonyl radical and thiyl radical was proposed on the basis of the previously reported references and mechanistic investigations. In addition, quantum chemical simulations revealed that Cu-promoted decomposition of sulfonyl hydrazides is thermodynamically viable in the developed conditions.
- Kim, Junsu,Park, Sanggil,Kim, Hyungjun,Kim, Jinho
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- S-(4-Methoxyphenyl)-4-methoxybenzenesulfonothioate as a Promising Lead Compound for the Development of a Renal Carcinoma Agent
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Organosulfur compounds show cytotoxic potential towards many tumor cell lines. Disulfides and thiosulfonates act through apoptotic processes, inducing proteins associated with apoptosis, endoplasmic reticulum stress, and the unfolded protein response. Three p-substituted symmetric diaryl disulfides and three diaryl thiosulfonates were synthesized and analyzed for inhibition of tubulin polymerization and for human cancer cell cytotoxic activity against seven tumor cell lines and a non-tumor cell line. S-(4-methoxyphenyl)-4-methoxybenzenesulfonothioate (6) exhibited inhibition of tubulin polymerization and showed the best antiproliferative potential, especially against the 786-0 cell line, being six times more selective as compared with the non-tumor cell line. In addition, compound 6 was able to activate caspase-3 after 24 and 48 h treatments of the 786-0 cell line and induced cell-cycle arrest in the G2/M stage at the highest concentration evaluated at 24 and 48 h. Compound 6 was able to cause complete inhibition of proliferation, inducing the death of 786-0 cells, by increasing the number of cells at G2/M and greater activation of caspase-3.
- Nantes, Camilla I.,Pereira, Ingrid D.,Bai, Ruoli,Hamel, Ernest,Burnett, James C.,de Oliveira, Rodrigo J.,de F. C. Matos, Maria,Beatriz, Adilson,Yonekawa, Murilo K. A.,Perdomo, Renata T.,de Lima, Dênis P.,Bogo, Danielle,dos A. dos Santos, Edson
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p. 449 - 458
(2020/01/25)
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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
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supporting information
p. 6600 - 6604
(2020/09/02)
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- TBAI-mediated sulfenylation of arenes with arylsulfonyl hydrazides in DPDME
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An efficient TBAI (tetrabutylammonium iodide)-mediated C–H sulfenylation of arenes with arylsulfonyl hydrazides in dipropylene glycol dimethyl ether (DPDME) was described. Various electron-rich arenes were applicable in the reaction, such as naphthylamine, naphthol, aniline, indole, pyrrole, and imidaz o [1,2-a] pyridine. A wide range of the aryl sulfides were obtained with good functional group tolerance. This method features green reaction conditions (odorless and easily available sulfur reagent, recyclable TBAI, and DPDME as solvent), and broad substrate scope. The synthetic potential is demonstrated by gram-scale synthesis and downstream transformations. The mechanism studies show that the reaction is achieved through electrophilic substitution process, and diaryl disulfide may be the main intermediate.
- Jie, Zhang,Jing, He,Ping, Liu,Xuezhen, Li,Yali, Liu,Yueting, Wei
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- Aerobic Copper-Catalyzed Synthesis of (E)-Vinyl Sulfones by Direct C-S Bond Oxidative Coupling
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Copper-catalyzed aerobic oxidative C-S bond coupling reaction between thiophenols and aryl-substituted alkenes for (E)-vinyl sulfones synthesis is reported here. With air utilized as a green oxidant, this transformation not only produces various vinyl sulfones in moderate to good yields but also possesses a simple and ecofriendly system. To clarify the mechanism, kinetic experiments has been investigated.
- Liang, Xiao,Xiong, Mingteng,Zhu, Heping,Shen, Kexin,Pan, Yuanjiang
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p. 11210 - 11218
(2019/09/12)
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- Relative Rates of Metal-Free Azide-Alkyne Cycloadditions: Tunability over 3 Orders of Magnitude
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The thermal (3 + 2) dipolar azide-alkyne cycloaddition, proceeding without copper or strained alkynes, is an underutilized ligation with potential applications in materials, bioorganic, and synthetic chemistry. Herein, we investigate the effects of alkyne substitution on the rate of this reaction, both experimentally and computationally. Electron-withdrawing groups accelerate the reaction, providing a range of relative rates from 1.0 to 2100 between the slowest and fastest alkynes studied. Unexpectedly, aryl groups conjugated to the alkyne significantly retard the reaction rate. In contrast, a sulfonyl, ester-substituted alkyne is reactive enough that it couples with an azide at room temperature in a few hours. This reactivity scale should provide a guide to those who wish to use this ligation under mild conditions.
- Skelly, Patrick W.,Sae-Jew, Jirapon,Kitos Vasconcelos, Ana Paula,Tasnim, Jerin,Li, Longbo,Raskatov, Jevgenij A.,Braslau, Rebecca
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- Cs2CO3-Mediated Vicinal Thiosulfonylation of 1,1-Dibromo-1-Alkenes with Thiosulfonates: An Expedient Synthesis of (E)-1,2-Thiosulfonylethenes
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A new and highly efficient vicinal thiosulfonylation of 1,1-dibromo-1-alkenes with thiosulfonates in the presence of cesium carbonate has been developed. The metal-free diheterofunctionalization is an operationally simple to access a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields with high levels of stereoselectivities. Further, scalable reactions have been demonstrated for this transformation, thus illustrating its efficiency and practicality. (Figure presented.).
- Reddy, Raju Jannapu,Kumari, Arram Haritha,Kumar, Jangam Jagadesh,Nanubolu, Jagadeesh Babu
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supporting information
p. 1587 - 1591
(2019/02/16)
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- Unprecedented Reactivity of β-Iodovinyl Sulfones: An Efficient Synthesis of β-Keto Sulfones and β-Keto Thiosulfones
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An unprecedented reactivity of (E)-β-iodovinyl sulfones in the presence of NaOAc is reported. The (E)-β-iodovinyl sulfones were treated with NaOAc in DMSO/H2O to yield β-keto sulfones in moderate to high yields. A novel oxidative difunctionalization of β-iodovinyl sulfones with thiosulfonates and NaOAc in DMF has been developed. This metal-free oxosulfenylation is an operationally simple to access a wide range of β-keto thiosulfones (α-thioaryl-β-keto sulfones) in moderate to high yields. The transformations were reliable at gram-scale, thus illustrating its efficiency and practicality. A plausible mechanism for the protocol is also proposed.
- Reddy, Raju Jannapu,Kumar, Jangam Jagadesh,Kumari, Arram Haritha
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supporting information
p. 3771 - 3775
(2019/06/24)
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- External Oxidant-Free Oxidative Tandem Cyclization: NaI-Catalyzed Thiolation for the Synthesis of 3-Thiosubstituted Pyrroles
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A simple method for the synthesis of 3-thiosubstituted pyrroles from homopropargylic amines and thiosulfonates via a tandem sulfenylation/cyclization has been developed. The thiosulfonates are used both as substrates and oxidants in this transformation. This procedure exhibits good functional group tolerance and a series of 3-thiosubstituted pyrrole derivatives was obtained in moderate to good yields. (Figure presented.).
- Yuan, Bingxiang,Jiang, Yong,Qi, Zhenjie,Guan, Xin,Wang, Ting,Yan, Rulong
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supporting information
p. 5112 - 5117
(2019/11/11)
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- Reactions between 5-Nitroso-1,3-diphenyltetrazolium salts and electron-rich arenes, amines, thiophenol, sulfoxides, and thioanisole
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A series of reactions between 5-nitroso-1,3-diphenyltetrazo-lium tetrafluoroborate and methoxybenzenes, amines, thiols, sulfoxides, and sulfides, most of which are generally accepted as being inert to nitroso groups, is reported here. The tetrazolium-activated nitroso functionality is capable of oxidizing the aforementioned substrates to give the corresponding oxidized products, and the nitroso tetrazolium itself is transformed into the corresponding amide or hydroxyamide, depending on the nature of the reaction partners. In the case of thioanisole, an addition product was obtained.
- Matsukawa, Yuta,Hirashita, Tsunehisa,Araki, Shuki
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supporting information
p. 540 - 544
(2019/04/05)
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- Gold/photoredox-cocatalyzed atom transfer thiosulfonylation of alkynes: Stereoselective synthesis of vinylsulfones
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We report a gold and photoredox combined radical approach for the rapid synthesis of thio-functionalized vinylsulfones from alkynes. Key features of this method include very mild conditions, broad substrate scope, excellent regio- and stereoselectivties, and 100% atom economy.
- Song, Tingting,Li, Haoyu,Wei, Fang,Tung, Chen-Ho,Xu, Zhenghu
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supporting information
p. 916 - 919
(2019/02/27)
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- Preparation method of thiosulfonate compounds in aqueous phase
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The invention relates to a preparation method of thiosulfonate compounds in an aqueous phase. The preparation method comprises adding sulfonyl hydrazide, an accelerant, an oxidant and solvent water into a Schlenk reaction bottle, stirring to allow to react under certain temperature and air atmosphere, and carrying out free radical coupling reaction to obtain the thiosulfonate compounds.
- -
-
Paragraph 0057-0059
(2019/06/27)
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- A S - aryl sulfur [...] compound synthesis method (by machine translation)
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The invention discloses a S - aryl sulfur [...] compound synthesis method, the method through in the organic solvent, phenyl four boron fluoride diazonium salt with thiourea to form phenyl isothiourea salt after the addition, thiophenol anion obtained, under the light source is illuminated, excited state of Rodamin 6 G will thiophenol anion thiophenol free radical oxidation; phenyl four boron fluoride diazonium salt with low valence state of Rodamin 6 G generating single electron transfer by the phenyl radical, phenyl radical with a solid substitute of the sulfur dioxide is obtained by combining the benzenesulfonyl radical; thiophenol radical with a benzenesulfonyl radical-radical coupling, to obtain the corresponding target product. The method of the invention mild condition, simple and efficient, the reaction yield is high, good product purity, facilitates separation of the purification, it has very good application value. (by machine translation)
- -
-
Paragraph 0023; 0024; 0026
(2019/01/23)
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- Nickel-Catalyzed Defluorinative Reductive Cross-Coupling Reaction of gem-Difluoroalkenes with Thiosulfonate or Selenium Sulfonate
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A nickel-catalyzed defluorinative reductive cross-coupling of gem-difluoroalkenes with thiosulfonate or selenosulfonates is described. The reaction involves the formation of thiolated or selenylated monofluoroolefins via regioselective C-F bond cleavage and C-S or C-Se bond formation and features easily available substrates, mild reaction conditions, and high E-selectivity. One of the derivatives by further cross coupling with PhMgBr exhibited an aggregation-induced emission enhancement effect.
- Li, Jian,Rao, Weidong,Wang, Shun-Yi,Ji, Shun-Jun
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p. 11542 - 11552
(2019/09/30)
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- Thermolysis-Induced Two- or Multicomponent Tandem Reactions Involving Isocyanides and Sulfenic-Acid-Generating Sulfoxides: Access to Diverse Sulfur-Containing Functional Scaffolds
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Direct reaction of isocyanides with some sulfenic-acid-generating sulfoxides led to the effective formation of the corresponding thiocarbamic acid S-esters in good to high yields. A multicomponent reaction involving isocyanide, sulfoxide, and a suitable nucleophile has also been developed, providing ready access to a diverse range of sulfur-containing compounds, including isothioureas, carbonimidothioic acid esters, and carboximidothioic acid esters.
- Wu, Shengfeng,Lei, Xiaofang,Fan, Erkang,Sun, Zhihua
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supporting information
p. 522 - 525
(2018/02/10)
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- Selective oxidation method of disulfide
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The invention relates to a selective oxidation method of disulfide, and discloses a novel synthesis method of a single sulfone compound shown as a formula (I). According to the invention, disulfide shown in a formula (II) is taken as a raw material, under existence of tert-butyl hydroperoxide, an oxidation reaction is carried out in a solvent, after the reaction is completed, and through post-treatment, the single sulfone compound shown as the formula (I) is obtained. Compared with the prior art, an oxidizing agent tert-butyl hydroperoxide which is friendly to environment is employed, usage ofa metal catalyst is avoided, the reaction condition is mild, selectivity is high, the operation is simple, the applicability is wide, and the reaction yield is high.
- -
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Paragraph 0024; 0025; 0026
(2018/09/26)
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- One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents
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Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.
- Fakhry, Jerome,Grayson, David H.
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p. 556 - 563
(2017/12/28)
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- Direct halosulfenylation of benzo[: B] furans: A metal-free synthesis of 3-halo-2-thiobenzo [b] furans
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The first example of the direct halosulfenylation of benzo[b]furans with commercially available disulfides and N-halosuccinimides has been achieved, providing an efficient metal-free synthetic pathway to access diverse 3-halo-2-thiobenzo[b]furans in moderate to excellent yields. In particular, a halogen (e.g., bromo or iodo) substituent on the benzo[b]furan ring is amenable for further synthetic elaborations thereby broadening the diversity of the products.
- Zhen, Qianqian,Huang, Dayun,Shao, Yinlin,Cheng, Tianxing,Chen, Jiuxi
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p. 9204 - 9210
(2019/01/03)
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- Transition-Metal-Free Synthesis of Thiosulfonates through Radical Coupling Reaction
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An efficient and practical transition-metal-free radical coupling reaction of sulfonyl hydrazides mediated by NIS/K 2 S 2 O 8 has been developed to afford a variety of biological activity thiosulfonates in moderate to excellent yields. Compared to a known approach for the synthesis of thiosulfonates from sulfonyl hydrazides, this strategy features high yields, mild reaction conditions, and broad substrate scope. The mechanistic studies revealed that the procedure undergoes via a radical cross-coupling process for the construction of S-S bonds.
- Zhou, Guodong,Xu, Xu-Dong,Chen, Gan-Ping,Wei, Wen-Ting,Guo, Zhiyong
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supporting information
p. 2076 - 2080
(2018/09/18)
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- Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3·OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates
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The BF3·OEt2-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O)2 bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.
- Cao, Liang,Luo, Shi-He,Jiang, Kai,Hao, Zhi-Feng,Wang, Bo-Wen,Pang, Chu-Ming,Wang, Zhao-Yang
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supporting information
p. 4754 - 4758
(2018/08/24)
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- H2O2-mediated metal-free protocol towards unsymmetrical thiosulfonates from sulfonyl hydrazides and disulfides in PEG-400
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A green and practical protocol between sulfonyl hydrazides and disulfides is herein reported for the synthesis of unsymmetrical thiosulfonates with the assistance of H2O2 in PEG-400, releasing N2 and H2O as the byproducts. The efficient and compatible process was considered to take place in the absence of metallic catalysts through a radical mechanism as determined by EPR analysis.
- Peng, Zhihong,Zheng, Xiao,Zhang, Yingjun,An, Delie,Dong, Wanrong
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supporting information
p. 1760 - 1764
(2018/04/30)
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- PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
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A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
- Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
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p. 2360 - 2364
(2018/05/24)
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- Amine Activation: N-Arylamino Acid Amide Synthesis from Isothioureas and Amino Acids
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N-arylamino acid amides have been synthesized via a novel method based on N-arylamine activation into isothioureas followed by reaction with amino acids under iron catalysis. The activated N-arylamines are easily prepared using a three-component reaction with commercial reagents, tert-butylisocyanide and S-phenyl benzenethiosulfonate. The protocol shows a broad functional group compatibility, with respect to side chain functionality of the amino acid (e. g. aliphatic and aromatic OH, (hetero)aromatic NH, amide NH, thioether), and the chiral amino acids do not undergo epimerization. The mechanism of the new amide synthesis has been studied. (Figure presented.).
- Zhu, Yan-Ping,Mampuys, Pieter,Sergeyev, Sergey,Ballet, Steven,Maes, Bert U. W.
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p. 2481 - 2498
(2017/07/22)
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- Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles
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Non-oxidative, regioselective, and convergent access to densely functionalized oxazoles is realized in a functional-group tolerant manner using alkynyl thioethers. Sulfur-terminated alkynes provide access to reactivity previously requiring strong donor-substituted alkynes such as ynamides. Sulfur does not act in an analogous donor fashion in this gold-catalyzed reaction, thus leading to complementary regioselective outcomes and addressing the limitations of using ynamides.
- Reddy, Raju Jannapu,Ball-Jones, Matthew P.,Davies, Paul W.
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supporting information
p. 13310 - 13313
(2017/10/07)
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- Tuning the Reactivity of Functionalized Diallylic Alcohols: Br?nsted versus Lewis Acid Catalysis
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The chemodivergent reactivity of bifunctional, enol thioether-containing diallylic alcohols in acidic medium is disclosed, highlighting the difference between strong Lewis acid and mild Br?nsted acid catalysis. In the presence of bismuth(III) triflate, allylic alcohol activation affords diversely substituted cyclopentenones in a Nazarov-type electrocyclization, whereas activation of the thioenol ether by p-toluenesulfonic acid provides an entry to α-sulfenylated β,γ-unsaturated ketones. Both methods represent a facile access to the corresponding products under mild conditions, using inexpensive and non-toxic catalytic systems.
- Lempenauer, Luisa,Du?ach, Elisabet,Lemière, Gilles
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supporting information
p. 10285 - 10288
(2017/08/07)
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- Visible-light-induced thiotrifluoromethylation of terminal alkenes with sodium triflinate and benzenesulfonothioates
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An unconventional reductive quenching cycle was developed to realize the visible-light-induced thiotrifluoromethylation of terminal alkenes. CF3SO2Na was used as an easy to handle CF3 radical source to afford the desired products in moderate to good yields. Mild reaction conditions and a broad substrate scope feature in this transformation.
- Kong, Weiguang,An, Hejun,Song, Qiuling
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supporting information
p. 8968 - 8971
(2017/08/15)
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- Visible light induced decomposition of sulfonyl hydrazides using Pd/ZrO2nanocomposite photocatalyst
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A new approach to synthesis of thiosulfonates has been developed under mild conditions without any oxidants and promoting reagents through a Pd/ZrO2nanocomposite photocatalyst catalyzed decomposition of sulfonyl hydrazides. This protocol gave the products in moderate yields, comparable to the best results reported so far. Finally, a plausible reaction mechanism was proposed.
- Li, Xiaoji,Zhou, Chao,Diao, Pinhui,Ge, Yanqin,Guo, Cheng
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supporting information
p. 1296 - 1300
(2017/03/10)
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- Non-expensive, open-flask and selective catalytic systems for the synthesis of sulfinate esters and thiosulfonates
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Two simple and efficient methods for the synthesis of sulfinate esters and thiosulfonates from sodium salts of sulfinic acids are described. Different alcohols were converted into the corresponding sulfinate esters in good yields and purity in an open flask. By the adjustment of the reaction conditions thiosulfonates could also be obtained in a very short reaction time.
- Tranquilino, Arisson,Andrade, Silvia R.C.P.,da Silva, Ana Paula M.,Menezes, Paulo H.,Oliveira, Roberta A.
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supporting information
p. 1265 - 1268
(2017/03/10)
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