cas 3112-90-1, BENZYL METHYL SULFONE | Articles data

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High Chemoselectivity in the Construction of Aryl Methyl Sulfones via an Unexpected C-S Bond Formation between Sulfonylhydrazides and Dimethyl Phosphite
A highly chemoselective route to aryl methyl sulfones via an unexpected C S bond formation between sulfonylhydrazides and dimethyl phosphite catalyzed by NaI under mild conditions has been established. This transformation provides an alternative and metal-free pathway to acquire various aryl methyl sulfones in good to excellent yields. Notably, dimethyl phosphite was employed as a stable and readily available alkyl source.
Liu, Teng,Yu, Shiwen,Shen, Xiang,Li, Yixian,Liu, Jianjun,Huang, Chao,Cheng, Feixiang
p. 153 - 160
(2021/10/04)

A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
supporting information
p. 156 - 161
(2021/01/14)

Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor-Acceptor Activation of Pyridinium Salts
Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO2 to generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chemistry relevant sulfonyl-containing motifs.
Andrews, Jonathan A.,Pantaine, Lo?c R. E.,Palmer, Christopher F.,Poole, Darren L.,Willis, Michael C.
supporting information
p. 8488 - 8493
(2021/11/01)

The mutagenesis of a single site for enhancing or reversing the enantio- or regiopreference of cyclohexanone monooxygenases
The mutagenesis of a "second sphere"switch residue of CHMOAcineto could control its enantio- and regiopreference. Replacing phenylalanine (F) at position 277 of CHMOAcineto into larger tryptophan (W) enabled a significant enhancement of enantio- or regioselectivity toward structurally diverse substrates, moreover, a complete reversal of enantio- or regiopreference was realized by mutating F277 into a range of smaller amino acids (A/C/D/E/G/H/I/K/L/M/N/P/Q/R/S/T/V).
Hu, Yujing,Xu, Weihua,Hui, Chenggong,Xu, Jian,Huang, Meilan,Lin, Xianfu,Wu, Qi
supporting information
p. 9356 - 9359
(2020/11/02)

An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity
A series of nine methyl sulphones (3a-3i) starting from the aldehydes (1a-1i) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols (2a-2i) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF3.Et2O in acetic acid medium at room temperature for about 2-3 h. The reaction conditions are simple, yields are high (85%-95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1H, 13C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.
Bollikolla, Hari Babu,Dasireddy, Chandra Rao,Kotra, Vijay,Ravi Kumar, Gollapudi,Varala, Ravi
p. 1386 - 1394
(2020/11/20)

Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates
A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).
Chen, Hongyi,Huang, Youming,Zeng, Qingle,Zheng, Wenting
(2020/08/28)

Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones
We report a facile synthesis of sulfones, β-keto sulfones, and sulfonamides from vinyl sulfones via an addition-elimination sequence where in situ generation of nucleophilic sulfinate ion is mediated by cyanide. The use vinyl sulfones renders high selectivity for S -alkylation to produce sulfones in high yields. In the presence of N -bromosuccinimide, primary and secondary amines underwent sulfonamide formation. A preliminary mechanistic study showed the formation of acrylonitrile as an innocent byproduct, without interfering with the desired reaction pathway while generating a sulfinate nucleophile.
Lee, Ji-Woong,Roy, Tamal
p. 455 - 458
(2020/03/13)

Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde
A tuneable metal-free protocol for the selective preparation of a-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. In this process, stable paraformaldehyde was used as the carbon source. The base played an important role in the selectivity control of transformations. More than 50 products were synthesized with excellent chemoselectivity and broad functional group tolerance.
Xiao, Fuhong,Hu, Yangling,Huang, Huawen,Xu, Fen,Deng, Guo-Jun
supporting information
p. 3527 - 3535
(2020/05/25)

Carbon nanotube-ruthenium hybrid towards mild oxidation of sulfides to sulfones: Efficient synthesis of diverse sulfonyl compounds
A heterogeneous catalyst was assembled with ruthenium nanoparticles on carbon nanotubes and used in a mild oxidation method to prepare sulfones from sulfides. The system proved very efficient on the investigated substrates and the products were obtained in high yields.
Almeida, Renata G.,De Carvalho, Renato L.,Nunes, Mateus P.,Gomes, Roberto S.,Pedrosa, Leandro F.,De Simone, Carlos A.,Gopi, Elumalai,Geertsen, Valérie,Gravel, Edmond,Doris, Eric,Da Silva Júnior, Eufranio N.
p. 2742 - 2748
(2019/06/17)

A novel synthesis of aryl methyl sulfones and β-hydroxysulfones from sodium sulfinates and di-tert-butyl peroxide in H2O medium
A novel and convenient synthetic route for aryl methyl sulfones and β-hydroxysulfones was developed via the radical reaction between sodium sulfinates and di-tert-butyl peroxide (DTBP). Without any catalysts and additives, the synthetic process could be smoothly carried out to afford the target products in good to excellent yields in H2O medium, demonstrating its promising application. In the present system, H2O could act not only as a green solvent but also as a reactant.
Lai, Junyi,Yuan, Gaoqing
supporting information
p. 524 - 527
(2018/01/10)

Green Organocatalytic Oxidation of Sulfides to Sulfoxides and Sulfones
A highly efficient synthetic methodology towards the selective synthesis of sulfoxides and sulfones is reported using a cheap and green organocatalytic method. Starting from sulfides and using 2,2,2-trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, the high-yielding preparation of sulfoxides or sulfones is described, being dependent on the reaction conditions.
Voutyritsa, Errika,Triandafillidi, Ierasia,Kokotos, Christoforos G.
p. 917 - 924
(2017/02/15)

An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor
A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented. Water is used as the source of oxygen to enable the oxidation process. The oxidation reaction utilizes the same reagents in all scenarios and the selectivity is solely governed by the applied potential. The procedure exhibits a broad scope and good functional group compatibility providing access to various sulfoxides (15 examples), sulfones (15 examples) and disulfides (6 examples). The use of continuous flow allows the optimal reaction parameters (e.g. residence time, applied voltage) to be rapidly assessed, to avoid mass- and heat-transfer limitations and to scale the electrochemistry.
Laudadio, Gabriele,Straathof, Natan J. W.,Lanting, Menno D.,Knoops, Benny,Hessel, Volker,No?l, Timothy
supporting information
p. 4061 - 4066
(2017/09/07)

Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions
Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.
Day, Jacob J.,Neill, Deshka L.,Xu, Shi,Xian, Ming
p. 3819 - 3822
(2017/07/26)

Sulfone compound (by machine translation)
[Problem] to safely and conveniently, highly selective, sulfide compound producing a sulfone compound. [Solution] pH is 9 - 12 under, water or water-insoluble solvent or an aromatic hydrocarbon-based solvent mixture, sodium hypochlorite is used as oxidizing agent, (1) (2) from the compound represented by the formula sulfide sulfone compound represented by the formula manufacturing method. (R1 And R2 Are each independently an alkyl, aryl, aralkyl, heteroaryl)[Drawing] no (by machine translation)
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Paragraph 0034; 0035

(2017/10/06)

Method for selectively compounding aryl methyl sulphone and belta-hydroxy sulphone derivative
The invention discloses a method for selectively compounding an aryl methyl sulphone and belta-hydroxy sulphone derivative. The method has the advantages that sulfinic acid sodium salt and di-tert-butyl peroxide serve as raw materials, water serves as green reaction solvent, additives and catalysts are not needed, and the aryl methyl sulphone and belta-hydroxy sulphone derivative is obtained through control of reaction temperature selectivity. The method has the advantages of mild reaction condition, simplicity in operation, low cost, environment friendliness, high product selectivity, high yield and the like, and has practical application value.
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Paragraph 0064; 0065; 0066

(2017/08/29)

Copper-catalyzed: S -methylation of sulfonyl hydrazides with TBHP for the synthesis of methyl sulfones in water
A copper-catalyzed S-methylation of sulfonyl hydrazides with TBHP was efficiently developed, providing a variety of methyl sulfones with good to excellent yields. The reaction can be carried out in water smoothly without any ligand or additive under mild conditions and this catalyst-in-water can be recycled several times.
Yang, Yu,Bao, Yajie,Guan, Qianqian,Sun, Qi,Zha, Zhenggen,Wang, Zhiyong
p. 112 - 116
(2017/08/15)

Efficient synthesis of aliphatic sulfones by Mg mediated coupling reactions of sulfonyl chlorides and aliphatic halides
Sulfonyl chlorides were reduced to anhydrous sulfinate salts with magnesium under sonication. These sulfinates were alkylated to sulfones with alkyl chlorides in the presence of catalytic sodium iodide under sonication. A variety of aliphatic sulfones was efficiently prepared by this one-pot two-step procedure.
Fu, Ying,Xu, Qin-Shan,Li, Quan-Zhou,Du, Zhengyin,Wang, Ke-Hu,Huang, Danfeng,Hu, Yulai
supporting information
p. 2841 - 2845
(2017/04/03)

Photoredox catalysis for oxygenation/deoxygenation between sulfides and sulfoxides by visible-light-responsive polyoxometalates
In this paper, we report the unique visible-light-responsive photoredox catalysis of a divacant lacunary silicotungstate TBA4H4[γ-SiW10O36] (SiW10) for functional group transformations of sulfur-containing compounds; namely, (i) aerobic oxygenation of sulfides to sulfoxides and (ii) deoxygenation of sulfoxides to sulfides. In the presence of suitable additives, such as Ce3+ (electron transfer mediator for oxygenation) and an alcohol (electron and proton donor for deoxygenation), SiW10 shows visible-light-induced charge transfers by using the newly formed highest occupied molecular orbitals derived from the coordinating Ce3+ or alcohol at the vacant site of SiW10. Consequently, oxygenation of sulfides and deoxygenation of sulfoxides can selectively proceed by irradiation with visible light (λ > 400 nm) to afford the corresponding desired products in high yields. The SiW10 photocatalysts can readily be recovered and reused for these transformations. Based on evidence from several experiments, the roles of the additives as well as the reaction mechanisms for these transformations are also discussed.
Suzuki, Kosuke,Jeong, Jinu,Yamaguchi, Kazuya,Mizuno, Noritaka
p. 1014 - 1021
(2016/02/19)

Polyoxomolybdate-Calix[4]arene Hybrid: A Catalyst for Sulfoxidation Reactions with Hydrogen Peroxide
An easily accessible polyoxomolybdate-calix[4]arene hybrid 1 has been synthesized and applied as a heterogeneous catalyst in the sulfoxidation of thioethers to sulfoxides and to sulfones under strictly stoichiometric amounts of 30% H2O2 in CH3CN as the solvent. This study represents the first promising example of successful employment of calixarenes-polyoxometalate (POM) hybrid materials in the area of catalytic oxidations.
Meninno, Sara,Parrella, Alessandro,Brancatelli, Giovanna,Geremia, Silvano,Gaeta, Carmine,Talotta, Carmen,Neri, Placido,Lattanzi, Alessandra
supporting information
p. 5100 - 5103
(2015/11/03)

Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: Rhodium-catalyzed double C-H activation controlled by different directing groups
A rhodium(III)-catalyzed cross-coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (C-H, C-S, O-H) and the formation of two bonds (C-C, C-O). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double C-H activation, the first of such examples in cross-oxidative coupling.
Zhang, Xi-Sha,Zhang, Yun-Fei,Li, Zhao-Wei,Luo, Fei-Xian,Shi, Zhang-Jie
supporting information
p. 5478 - 5482
(2015/04/27)

Extreme synergistic mutational effects in the directed evolution of a baeyer-villiger monooxygenase as catalyst for asymmetric sulfoxidation
Structure-based directed evolution utilizing iterative saturation mutagenesis (ISM) has been applied to phenyl acetone monooxygenase (PAMO), a thermally robust Baeyer-Villiger monooxygenase, in the quest to access a mutant which displays reversed enantioselectivity in the asymmetric sulfoxidation of prochiral thioethers. Whereas WT PAMO leads to 90% ee in the sulfoxidation of p-methylbenzyl methyl thioether with preference for the (S)-sulfoxide, the evolved mutant I67Q/P440F/A442N/L443I is 95% (R)-selective in the reaction of this and other thioethers. Partial deconvolution of the (R)-selective mutant with generation of the respective four single mutants shows that all of them are (S)-selective, which points to pronounced synergism (cooperative nonadditivity) when they interact in concert. Complete deconvolution with formation of all combinatorial forms of the respective double and triple mutants allows the designed construction of a fitness landscape featuring all 24 upward pathways leading from WT to the (R)-selective quadruple mutant. In all 24 trajectories strong cooperative mutational effects were found as well, which indicates that such mutational changes in enzymes constitute nonlinear systems. A theoretical analysis based on induced fit docking explains many of the observed effects on a molecular level.
Zhang, Zhi-Gang,Lonsdale, Richard,Sanchis, Joaquin,Reetz, Manfred T.
p. 17262 - 17272
(2015/02/19)

Synthesis of arylethyl (E)-styrylsulfones and arylsulfones by one-pot DIBAL-H/NaH-mediated reaction of β-ketosulfones
A facile one-pot synthetic route for preparing a series of arylethyl (E)-styrylsulfones or arylethyl arylsulfones is developed. The efficient one-pot DIBAL-H/NaH-mediated route includes reduction of α-benzyl-β- arylketosulfones and retroaldol/aldol or retro aldol reaction of the resulting intermediate. The DIBAL-H/NaH-mediated reaction mechanism has been discussed. Georg Thieme Verlag Stuttgart. New York.
Chang, Meng-Yang,Chen, Yi-Chia,Chan, Chieh-Kai
p. 1739 - 1744
(2014/08/05)

CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides
In this study, a facile CuI catalyzed synthesis of sulfones involving a nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides is realized. This reaction proceeds efficiently at room temperature, giving rise to various functional group substituted sulfones, generally in moderate to high yields. The method provides a novel, simple, and promising strategy for functionalized sulfone synthesis in the research field of sulfur chemistry. the Partner Organisations 2014.
Fu, Ying,Zhu, Wenbo,Zhao, Xingling,Huegel, Helmut,Wu, Zhouqiang,Su, Yuhu,Du, Zhengyin,Huang, Danfeng,Hu, Yulai
p. 4295 - 4299
(2014/06/23)

One-pot synthesis of multifunctionalized cyclopropanes
A facile one-step synthetic protocol toward multifunctionalized cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a [2C+1C] annulation.
Chang, Meng-Yang,Chen, Yi-Chia,Chan, Chieh-Kai
p. 2257 - 2263
(2014/03/21)

Sulfoxidation on a SiO2-supported Ru complex using O 2/aldehyde system
A site-isolated SiO2-supported Ru-monomer complex, whose structure was characterized by means of solid-state NMR, XPS, UV/vis, and Ru K-edge EXAFS, was found to be efficient for sulfoxidation using an O 2/aldehyde system. Significant enhancement of sulfoxidation rates was observed on the SiO2-supported Ru complex for various sulfide derivatives.
Maity, Niladri,Wattanakit, Chularat,Muratsugu, Satoshi,Ishiguro, Nozomu,Yang, Yong,Ohkoshi, Shin-Ichi,Tada, Mizuki
supporting information; experimental part
p. 4558 - 4565
(2012/07/02)

Sulfoxidation with hydrogen peroxide catalyzed by [SeO 4{WO(O2)2}2]2-
The selenium-containing dinuclear peroxotungstate, [(n-C4H 9)4N]2[SeO4{WO(O2) 2}2] (I), acts as a homogeneous catalyst for the selective oxidation of various kinds of cyclic mono- and disulfides with 30% aqueous H2O2. The cyclic disulfides were selectively oxidized to the corresponding monosulfoxides with one equivalent of H2O 2 with respect to the sulfides. In the presence of two equivalents of H2O2, the oxidation of dibenzothiophene gave the corresponding sulfone in 98% yield under the mild conditions. The negative Hammett ρ value (-0.62) for the competitive oxidation of p-substituted thioanisoles and the low XSO (XSO = (nucleophilic oxidation)/(total oxidation)) value of 0.14 for the I-catalyzed oxidation of thianthrene 5-oxide (SSO) revealed that I is a strong electrophilic oxidant. The reactivities of the di- and tetranuclear peroxotungstates with XO 4n- ligands (X = Se(vi), As(v), P(v), S(vi), and Si(iv)) were strongly dependent on the kinds of hetero atoms. The reaction rates for the sulfoxidation decreased with an increase in the XSO values and a peroxotungstate with a stronger electrophilicity was more active for the sulfoxidation. The kinetic and mechanistic investigations showed that the electrophilic attack of the peroxo oxygen at the sulfur atom is a key step in the sulfoxidation. The computational investigation supported the high chemoselectivitiy for the sulfoxidation of diallyl sulfide.
Kamata, Keigo,Hirano, Tomohisa,Ishimoto, Ryo,Mizuno, Noritaka
supporting information; experimental part
p. 5509 - 5518
(2010/08/04)

Tantalum carbide or niobium carbide catalyzed oxidation of sulfides with hydrogen peroxide: Highly efficient and chemoselective syntheses of sulfoxides and sulfones
The oxidation of sulfides with 30% hydrogen peroxide catalyzed by tantalum carbide provided the corresponding sulfoxides in high yields. The reaction of sulfides with 30% hydrogen peroxide catalyzed by niobium carbide efficiently afforded the corresponding sulfones. These catalysts can easily be recovered from the reaction mixture and may be repeatedly used as catalysts for the oxidation without losing their activity. Georg Thieme Verlag Stuttgart New York.
Kirihara, Masayuki,Itou, Atsushi,Noguchi, Takuya,Yamamoto, Junya
experimental part
p. 1557 - 1561
(2010/09/05)

Highly efficient oxidation of sulfides with hydrogen peroxide catalyzed by [SeO4{WO(O2)2}2]2-
By using the selenium-containing dinuclear peroxotungstate at 0.005-0.1 mol%, various kinds of sulfides could be converted into the corresponding sulfoxides or sulfones in excellent yields with one or two equivalents of H 2O2 with respect to the sulfide, respectively.
Kamata, Keigo,Hirano, Tomohisa,Mizuno, Noritaka
supporting information; experimental part
p. 3958 - 3960
(2010/01/06)

Tantalum(V) or niobium(V) catalyzed oxidation of sulfides with 30% hydrogen peroxide
Tantalum(V) and niobium(V) are effective catalysts for the oxidation of sulfides with 30% hydrogen peroxide. The reaction of sulfides with 30% hydrogen peroxide catalyzed by tantalum(V) chloride or niobium(V) chloride in acetonitrile, i-propanol or t-butanol selectively provided the corresponding sulfoxides in high yields. The corresponding sulfones are efficiently obtained from the reaction of sulfides with 30% hydrogen peroxide in methanol catalyzed by tantalum(V) or niobium(V).
Kirihara, Masayuki,Yamamoto, Junya,Noguchi, Takuya,Itou, Atsushi,Naito, Sayuri,Hirai, Yoshiro
experimental part
p. 10477 - 10484
(2010/02/28)

Tetra-(tetraalkylammonium)octamolybdate catalysts for selective oxidation of sulfides to sulfoxides with hydrogen peroxide
Tetra-(tetraalkylammonium)octamolybdate catalysts are successfully applied in the selective oxidation of various sulfides to sulfoxides with 30% aqueous hydrogen peroxide as oxidant under mild reaction conditions in 94-100% yield and 95-100% selectivity. The octamolybdate catalysts show high catalytic activity in a high ratio of substrate to catalyst (up to 10000:1) and are recyclable, with actively functional groups, including hydroxyl group and CC bonds, tolerated in the oxidation. The Royal Society of Chemistry 2009.
Yang, Chuanbo,Jin, Qingping,Zhang, Hua,Liao, Jian,Zhu, Jin,Yu, Bin,Deng, Jingen
supporting information; experimental part
p. 1401 - 1405
(2010/05/02)

Selective synthesis of sulfoxides and sulfones by tantalum(V) catalyzed oxidation of sulfides with 30% hydrogen peroxide
The reaction of sulfides with 30% hydrogen peroxide catalyzed by tantalum(V) chloride in acetonitrile, i-propanol, or t-butanol selectively provided the corresponding sulfoxides in high yields. On the other hand, the reaction of sulfides with 30% hydrogen peroxide-catalyzed by tantalum(V) chloride or tantalum(V) ethoxide in methanol effectively gave the sulfones.
Kirihara, Masayuki,Yamamoto, Junya,Noguchi, Takuya,Hirai, Yoshiro
scheme or table
p. 1180 - 1183
(2009/06/28)

Asymmetric oxidation of sulfides under solvent-free or highly concentrated conditions
The aluminium(salalen) complex was found to be an efficient catalyst for the asymmetric oxidation of sulfides under solvent-free or highly concentrated conditions, in which an only 0.002-0.01 mol% catalyst loading was sufficient to obtain optically active sulfoxides in high yield with high enantioselectivity. The Royal Society of Chemistry.
Matsumoto, Kazuhiro,Yamaguchi, Tetsufumi,Katsuki, Tsutomu
p. 1704 - 1706
(2008/12/22)

Highly selective 30% hydrogen peroxide oxidation of sulfides to sulfoxides using micromixing
The highly selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide has been achieved under catalyst-free conditions using a T-shaped micromixer. The Royal Society of Chemistry.
Noguchi, Takuya,Hirai, Yoshiro,Kirihara, Masayuki
scheme or table
p. 3040 - 3042
(2009/02/04)

Oxidoperoxidotungsten(VI) complexes with secondary hydroxamic acids: Synthesis, structure and catalytic uses in highly efficient, selective and ecologically benign oxidation of olefins, alcohols, sulfides and amines with H2O2 as a terminal oxidant
The reaction of a solution of freshly precipitated WO3 in H 2O2 separately with the secondary hydroxamic acids N-benzoyl-N-phenylhydroxamic acid (BPHAH), N-benzoyl-Northo-tolylhydroxamic acid (BOTHAH), N-benzoyl-N-meta-tolylhydroxamic acid (BMTHAH), N-benzoyl-N-para- tolyl-hydroxamic acid (BPTHAH) and N-cinnamyl-N-phenylhy-droxamic acid (CPHAH) afforded [WO(O2)(BPHA)2] (1), [WO(O2)(BOTHA) 2] (2), [WO(O2)(BMTHA)2] (3), [WO(O 2)-(BPTHA)2] (4) and [WO(O2)(CPHA)2] (5), respectively. Aqueous tungstate solution, on reaction with all these hydroxamic acids, produced [W(O)2(hydroxamato)2] (6). The complexes show excellent catalytic functions in the oxidation of (a) olefins at room temperature in the presence of NaHCO3 as promoter, (b) alcohols, sulfides and amines, at reflux, with H2O2 as a terminal oxidant, yielding a high turnover number (TON), the highest being for olefin-to-epoxide conversion. An attempt to synthesize peroxide-rich complexes of the type PPh4[WO(O2)2(hydroxamato)] (7), for example PPh4[WO-(O2)2BMTHA] (7C), resulted in the isolation of PPh4[WO-(O2)2(C 6H5COO)] (8), which was probably obtained by the hydrolysis of coordinated BMTHA. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Maiti, Swarup K.,Dinda, Subhajit,Banerjee, Surajit,Mukherjee, Alok K.,Bhattacharyya, Ramgopal
experimental part
p. 2038 - 2051
(2009/03/11)

Enantioselective sulfoxidation and kinetic resolution combined protocol mediated by a functionalized (S)-norcamphor-based hydroperoxide/titanium(IV) isopropoxide system
A functionalized tertiary furyl hydroperoxide derived from (S)-norcamphor has been easily synthesized in good yield and in a highly diastereoselective manner. Good to high enantioselectivities (up to 99% ee) and acceptable to good yields (up to 86%) were achieved for the sulfoxides, by tandem stereoconvergent asymmetric sulfoxidation and kinetic resolution when using the novel hydroperoxide s oxygen donor and chirality source in the presence of catalytic loadings of titanium(IV) isopropoxide as the catalyst.
Lattanzi, Alessandra,Piccirillo, Sandro,Scettri, Arrigo
p. 357 - 363
(2008/02/07)

Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water
A new chiral Fe(salan) complex was synthesized, and it was found to serve as an efficient catalyst for asymmetric oxidation of sulfides using hydrogen peroxide in water without surfactant. Not only alkyl aryl sulfides but also various methyl alkyl sulfides were oxidized to the corresponding sulfoxides with high enantioselectivities up to 96% ee. It should be noted that the turnover number of complex 4 amounts to 8000. Copyright
Egami, Hiromichi,Katsuki, Tsutomu
p. 8940 - 8941
(2008/02/11)

Oxidation of prochiral sulfides with chiral dioxirane
Dioxirane generated in situ by reaction of chiral 1,2:4,5-di-O- isopropylidene-D-erythro-hexo-2,4-diulo-2,6-pyranose with Oxone oxidizes prochiral sulfides to the corresponding sulfoxides with an enantiomeric excess of 2 to 25%. Pleiades Publishing, Inc., 2006.
Dieva,Eliseenkova,Efremov,Sharafutdinova,Bredikhin
p. 12 - 16
(2007/10/03)

Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation
Enantioselective vanadium-catalysed oxidation of aryl benzyl sulfides using Bolm's procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90% ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Kelly, Padraig,Lawrence, Simon E.,Maguire, Anita R.
p. 4500 - 4509
(2007/10/03)

Kinetic resolution in vanadium-catalyzed sulfur oxidation as an efficient route to enantiopure aryl benzyl sulfoxides
Enantiopure aryl benzyl sulfoxides can be prepared using vanadium-Schiff base catalyzed sulfide oxidation and kinetic resolution of the resulting sulfoxide. The kinetic resolution can be effected in combination with asymmetric sulfide oxidation or instead starting from the racemic sulfoxide. Georg Thieme Verlag Stuttgart.
Kelly, Pádraig,Lawrence, Simon E.,Maguire, Anita R.
p. 1569 - 1573
(2007/10/03)

Revisiting nucleophilic substitution reactions: Microwave-assisted synthesis of azides, thiocyanates, and sulfones in an aqueous medium
A practical, rapid, and efficient microwave (MW) promoted synthesis of various azides, thiocyanates, and sulfones is described in an aqueous medium. This general and expeditious MW-enhanced nucleophilic substitution approach uses easily accessible starting materials such as halides or tosylates in reaction with alkali azides, thiocyanates, or sulfinates in the absence of any phase-transfer catalyst, and a variety of reactive functional groups are tolerated.
Ju, Yuhong,Kumar, Dalip,Varma, Rajender S.
p. 6697 - 6700
(2007/10/03)

Selective oxidation of sulfides to sulfoxides and sulfones at room temperature using H2O2 and a Mo(VI) salt as catalyst
Selective oxidation of sulfides to sulfoxides and sulfones is achieved by H2O2 using MoO2Cl2 as the catalyst. Various substituted sulfides having functional groups such as methyl, methoxy, bromo, nitro, alkene, alkyne, alcohol, ester, aldehyde and remarkably an oxime are successfully and selectively oxidized without affecting the sensitive functionalities.
Jeyakumar, Kandasamy,Chand, Dillip Kumar
p. 4573 - 4576
(2007/10/03)

Oxoperoxo molybdenum(VI) and tungsten(VI) and oxodiperoxo molybdate(VI) and tungstate(VI) complexes with 8-quinolinol: Synthesis, structure and catalytic activity
A solution obtained by dissolving MoO3 in a moderate excess of H2O2 reacts with 8-quinolinol (QOH) to give [MoO(O 2)(QO)2] (1), but, when the same reaction is conducted with a large excess of H2O2, an anionic complex is formed, which reacts with PPh4Cl to give the corresponding salt [MoO(O 2)2(QO)][PPh4] (2 · PPh4). Freshly prepared WO3 behaves the same way and, depending on the amount of H2O2 used, as above, produces either [WO(O 2)(QO)2] (3) or [WO(O2)2(QO)] [PPh4] (4 · PPh4), respectively. Crystallographic analyses reveal the coordination geometries around the metal center in these complexes to be distorted pentagonal bipyramids. These compounds show interesting catalytic properties in the oxidation of alcohols using H 2O2 as the terminal oxidant. In the case of aromatics, including benzylic and cinnamylic alcohols, the oxidation occurs selectively, affording aldehydes or ketones with reasonably high turnover numbers. Taking benzyl alcohol as a representative case, a probable mechanism of the alcohol-to-aldehyde conversion mediated by the prepared catalysts is suggested. The oxidation of aliphatic primary alcohols, under the same conditions, does not show the above selectivity: the reaction yields the corresponding aldehydes as well as carboxylic acids. The work was also extended to study the catalytic activity towards the oxidation of phenol and various sulfides and amines using the same oxidants. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
Maiti, Swarup K.,Banerjee, Surajit,Mukherjee, Alok K.,Abdul Malik,Bhattacharyya, Ramgopal
p. 554 - 563
(2007/10/03)

Oxidations catalyzed by phenylacetone monooxygenase from Thermobifida fusca
Several organic sulfides, ketones and other organic systems have been tested as substrates in oxidation reactions catalyzed by the recently discovered phenylacetone monooxygenase from Thermobifida fusca. The biocatalytic properties of this Baeyer-Villiger monooxygenase have been studied, revealing reactivity with a large range of sulfides and ketones. Oxidations of several sulfoxides, an amine and an organoboron compound were also observed. The enzyme is able to oxidize a number of sulfides with excellent enantioselectivity, demonstrating the catalytic potential of this novel biocatalyst.
De Gonzalo, Gonzalo,Torres Pazmino, Daniel E.,Ottolina, Gianluca,Fraaije, Marco W.,Carrea, Giacomo
p. 3077 - 3083
(2007/10/03)

Tetrabutylammonium phosphomolybdate on fluorapatite: An efficient solid catalyst for solvent-free selective oxidation of sulfides
A new synthetic method of sulfoxides and sulfones using solvent-free oxidations of sulfides with urea-hydrogen peroxide complex (urea-H 2O2) and tetrabutylammonium phosphomolybdate catalyst on fluorapatite ((Bu4N)3[PMo12O 40]/FAp). In the solid-phase system the oxidations of aromatic and alkyl sulfides proceeded at 4-25°C and the corresponding sulfoxides or sulfones were selectively obtained in good yields by controlling the amount of urea-H2O2.
Sasaki, Yoh,Ushimaru, Kyohei,Iteya, Katsuma,Nakayama, Hirokazu,Yamaguchi, Shunro,Ichihara, Junko
p. 9513 - 9515
(2007/10/03)

Novel synthesis of sulfones from α,α-dibromomethyl aromatics
A novel, high yielding preparation of sulfones from α,α-dibromomethyl aromatics through reaction with a sulfinate salt is reported.
Xu, Feng,Savary, Kimberly,Williams, J. Michael,Grabowski, Edward J. J.,Reider, Paul J.
p. 1283 - 1286
(2007/10/03)

New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions
Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)-furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used as oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)4/L-DET or Ti(O-i-Pr)4/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomerically enriched Ti(IV)/BINOL/H2O complexes.
Massa, Antonio,Siniscalchi, Francesca R.,Bugatti, Valeria,Lattanzi, Alessandra,Scettri, Arrigo
p. 1277 - 1283
(2007/10/03)

Aluminum chloride-iron promoted coupling of sulfonyl chlorides with alkyl halides in aqueous media
A simple and inexpensive procedure for the coupling of sulfonyl chlorides and alkyl halides with aluminum chloride-iron system at ambient temperature in high yield is achieved in aqueous media.
Saikia, Promod,Laskar, Dhrubojyoti D.,Prajapati, Dipak,Sandhu, Jagir S.
p. 512 - 513
(2007/10/03)

A mild and efficient procedure for the oxidation of organic sulfides to sulfones by use of urea-hydrogen peroxide/trifluoroacetic anhydride system
Selective, mild and safe oxidation of dialkyl-, diaryl- and alkyl-aryl sulfides to the corresponding sulfones was achieved by using of urea- H2O2/trifluoroacetic anhydride system.
Balicki, Roman
p. 2235 - 2239
(2007/10/03)

Titanium-Catalyzed, Asymmetric Sulfoxidation of Alkyl Aryl Sulfides with Optically Active Hydroperoxides
The Ti-catalyzed, asymmetric oxidation of alkyl aryl sulfides by enantiomerically pure hydroperoxides (ee >99%) has been examined. Enantioselectivities with ee values up to ca. 80% were achieved for the oxygen transfer from (S)-(-)-1-phenylethyl hydroperoxide 2a to methyl phenyl and methyl p-tolyl sulfide 1a in CCl4 as solvent, but with much overoxidation to the corresponding sulfone 4. Detailed mechanistic studies showed that the enantioselectivity of the sulfide 1a oxidation results from a combination of a rather low (ee values >20%) asymmetric induction in the sulfoxidation and an effective kinetic resolution (ee values ca. 80% at 85% sulfide conversion) of the sulfoxide 3a by enantioselective oxidation to the sulfone 4a. The overoxidation (loss of chemoselectivity) is due to sulfoxide coordination to the Ti metal to generate a template in which the oxygen atom is intramolecularly transferred from the bound and activated, optically active hydroperoxide to the ligated sulfoxide in a stereocontrolled manner.
Adam, Waldemar,Korb, Marion N.,Roschmann, Konrad J.,Saha-Moeller, Chantu R.
p. 3423 - 3428
(2007/10/03)