- Highly selective oxidation of sulfides on a CdS/C3N4 catalyst with dioxygen under visible-light irradiation
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A CdS/C3N4 composite photocatalyst was fabricated by a facile method, and its structure, composition, and morphology were characterized in detail. The catalyst exhibited high photocatalytic product selectivity towards the oxidation o
- Xu, Yong,Fu, Zi-Cheng,Cao, Shuang,Chen, Yong,Fu, Wen-Fu
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- IMPORTANCE OF SINGLE ELECTRON-TRANSFER IN SINGLET OXYGEN REACTION IN AQUEOUS SOLUTION. OXIDATION OF ELECTRON-RICH THIOANISOLES
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Oxidation of substituted thioanisoles by chemically generated singlet oxygen was investigated in polar aqueous media.The formation of the superoxide ion was observed during sulphoxidation of 4-hydroxythioanisole (4) in phosphate buffer at pH 7.5.Control e
- Inoue, Kenzo,Matsuura, Teruo,Saito, Isao
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- Flavin-catalyzed aerobic oxidation of sulfides in aqueous media
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An aerobic, organocatalytic, and aqueous method for the oxidation of sulfides is described. Synthetic flavin, 5-ethyl-3,7,8,10- tetramethylisoalloxazinium perchlorate, acts as an efficient catalyst for the oxidation of sulfides in water under an oxygen atmosphere (1 atm) with the assistance of ascorbic acid as a reductant. This is an inexpensive, convenient, and environmentally benign method for the selective oxidative transformation of sulfides into sulfoxides.
- Imada, Yasushi,Kitagawa, Takahiro,Wang, Han-Kun,Komiya, Naruyoshi,Naota, Takeshi
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- Facile and selective oxidation of sulfides to sulfoxides by t-butyl hydroperoxide in aqueous medium
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The oxidation of sulfides to sulfoxides with TBHP in water only occurs selectively with high yields and permits the sulfoxides to be prepared without using organic solvents. When the reaction is performed in aqueous sulfuric acid with a H2SOsu
- Fringuelli,Pellegrino,Pizzo
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Read Online
- Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations
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Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.
- Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo
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supporting information
p. 7738 - 7744
(2021/05/07)
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- Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
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We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.
- Zhao, Bin,Hammond, Gerald B.,Xu, Bo
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supporting information
(2021/09/13)
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- In situconstruction of phenanthroline-based cationic radical porous hybrid polymers for metal-free heterogeneous catalysis
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Rational design of multifunctional radical porous polymers with redox activity for targeted metal-free heterogeneous catalysis is an important research topic. In this work, we reported a new class of phenanthroline-based cationic radical porous hybrid polymers (Phen˙+-PHPs), which were constructed from the Heck reaction between a newly designed dibromo-substituted phenanthroline ionic monomer (iDBPhen) and a rigid building block, octavinylsilsesquioxane (VPOSS). For the first time, the stable phenanthroline-based radical cation was unexpectedly discovered in these polyhedral oligomeric silsesquioxane (POSS)-based porous hybrid polymers, probably undergoingin situreduction of the dicationic monomer iDBPhen during the alkaline reagent K2CO3-involved Heck reaction. The radical characters of the typical porous polymers Phen˙+-PHP-2 and Phen˙+-PHP-2Br were confirmed from the electron paramagnetic resonance (EPR) spectra and X-ray photoelectron spectra (XPS). The chemical structures and porous geometry were fully characterized by a series of advanced technologies. Surprisingly, the metal-free cationic radical polymer Phen˙+-PHP-2 exhibited high heterogeneous catalytic efficiency in the H2O2-mediated selective oxidation of various sulfides to sulfoxides with high yields under mild conditions, owing to the electron-accepting and redox ability of Phen-based dications and radical cations. Moreover, the extended sample Phen˙+-PHP-2Br prepared by post-treatment of Phen˙+-PHP-2 with aqueous HBr was also employed as a metal-free efficient heterogeneous catalyst in the conversion of CO2with epoxides into cyclic carbonates under atmospheric pressure and low temperatures. The remarkable catalytic performance in CO2conversion should be assigned to the synergistic catalysis of POSS-derived Si-OH groups and nucleophilic Br?anions and N active atom-involved Phen cationic radical moieties within Phen˙+-PHP-2Br. These two catalysts can be facilely recovered and reused, also with stable recyclability in the above catalytic reaction systems, achieving the heterogeneous catalytic demands for multipurpose reactions.
- Chen, Guojian,Zhang, Yadong,Liu, Ke,Liu, Xiaoqing,Wu, Lei,Zhong, Hu,Dang, Xuejing,Tong, Minman,Long, Zhouyang
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supporting information
p. 7556 - 7565
(2021/04/06)
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- B2cat2-Mediated Reduction of Sulfoxides to Sulfides
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An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B2cat2) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.
- Takahashi, Fumiya,Nogi, Keisuke,Yorimitsu, Hideki
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supporting information
p. 3009 - 3012
(2020/03/25)
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- Vanadium oxides anchored on nitrogen-incorporated carbon: An efficient heterogeneous catalyst for the selective oxidation of sulfide to sulfoxide
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A highly efficient and durable metal catalyst stabilized by proper support is vital for organic catalytic transformations. In this study, a sequential pyrolysis–acid etching strategy was reported to prepare a nitrogen-rich nanocarbon inlaid with vanadium
- Fu, Yanghe,Qi, Yanyan,Tu, Gaomei,Xu, Qionghao,Zhang, Fumin,Zhu, Weidong
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- High-efficiency photo-oxidation of thioethers over C60?PCN-222 under air
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The selective oxidation of primary thioethers to sulfoxides is an important reaction in the production of pharmaceuticals, agrochemicals, and other valuable fine chemicals. However, the achievement of high conversion and selectivity towards sulfoxide duri
- Zheng, Deng-Yue,Chen, En-Xuan,Ye, Chun-Rong,Huang, Xiao-Chun
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p. 22084 - 22091
(2019/10/11)
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- Electrochemical synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide
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A new route for a one-pot synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide using an electrochemical technique was developed. This protocol proceeded smoothly by employing electrons and hydrogen peroxide as clean oxidants, and a wide range of aromatic and aliphatic sulfoxides were synthesized in moderate to good yields.
- Du, Ke-Si,Huang, Jing-Mei
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supporting information
p. 1405 - 1411
(2018/03/27)
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- A highly efficient reusable homogeneous copper catalyst for the selective aerobic oxygenation sulfides to sulfoxides
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Readily available copper showed efficient activity and great selectivity for the homogeneous catalysis of oxidation of sulfides to sulfoxides using molecular oxygen as the oxidant. The reaction proceeds under mild conditions in the presence of a catalytic amount of TEMPO. Importantly, the catalysts could be conveniently recovered and reused. And this methodology was proved to be applicable for the transformation of various aromatic and aliphatic sulfides into the corresponding sulfoxides with high conversion and high selectivity.
- Ren, Cheng,Fang, Runxing,Yu, Xiaochun,Wang, Shun
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supporting information
p. 982 - 986
(2018/02/13)
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- Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides
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Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.
- Gan, Shaoyan,Yin, Junjie,Yao, Yuan,Liu, Yang,Chang, Denghu,Zhu, Dan,Shi, Lei
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supporting information
p. 2647 - 2654
(2017/04/03)
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- Synthesis method of aryl sulfoxide compound
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The invention relates to a synthesis method of an aryl sulfoxide compound shown in the following formula (II). The synthesis method comprises the steps as follows: a compound shown in formula (I) is subjected to a catalytic oxidation reaction by using a c
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Paragraph 0056; 0057; 0058; 0059; 0060; 0111; 0116; 0121
(2017/07/20)
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- A chemoselective ipso-hydroxylation of arylboronic acids using urea-hydrogen peroxide under catalyst free condition
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An efficient and practical method for the chemoselective ipso-hydroxylation of arylboronic acids is demonstrated using urea-hydrogen peroxide under catalyst free condition at room temperature. Remarkably, oxidation sensitive functional groups such as olefin, aldehyde, alcohol, ketone, and sulfide as well as heterocycles such as pyridine and thiophene were tolerated under the standard reaction condition. In addition to the solution phase, a solid phase ipso-hydroxylation of arylboronic acids has been investigated with urea hydrogen peroxide. The scope and limitations of the solid phase protocol is discussed.
- Gupta, Surabhi,Chaudhary, Priyanka,Srivastava, Vandana,Kandasamy, Jeyakumar
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supporting information
p. 2506 - 2510
(2016/05/24)
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- An organic-inorganic hybrid supramolecular framework material based on a [P2W18O62]6- cluster and Yb & Na complexes of pyridine-2,6-dicarboxylic acid: A catalyst for selective oxidation of sulfides in water with H2O2
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A rare-earth-containing polyoxometalate (RECP) hybrid, {(Yb (PDCH2)2(PDCH))·Na(H2O)2·(Na(PDCH)(H2O)2)}2[P2W18O62]·14H2O (1), based on [P2W18O62]6- cluster anions and cationic Yb & Na complex units of pyridine-2,6-dicarboxylic acid (PDCH2) has been synthesized under normal reaction conditions, which exhibited a supramolecular 3-D framework structure in the crystal lattice. Hybrid 1 acts as a green catalyst for the selective oxidation of sulfides in water with H2O2 as the reagent.
- Reddy, Pulikanti Guruprasad,Mamidi, Narsimha,Pradeep, Chullikkattil P.
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p. 4272 - 4276
(2016/07/06)
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- SULFOXIDATION CATALYSTS AND METHODS FOR THEIR PREPARATION AND USE
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Methods and compositions of catalysts for sulfoxidation reaction processes are disclosed. The sulfoxidation reaction process can be performed in an aqueous medium, and the catalysts can be recycled for further use. In some embodiments, a method of making a catalyst may include contacting a transition metal compound with an oxidizing agent to form a first solution, contacting a carboxylic acid compound with a cationic surfactant to form a second solution, mixing the first solution and the second solution to form a precipitate, and isolating the precipitate.
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Paragraph 0054; 055
(2016/09/26)
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- Electron-deficient heteroarenium salts: An organocatalytic tool for activation of hydrogen peroxide in oxidations
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A series of monosubstituted pyrimidinium and pyrazinium triflates and 3,5-disubstituted pyridinium triflates were prepared and tested as simple catalysts of oxidations with hydrogen peroxide, using sulfoxidation as a model reaction. Their catalytic efficiency strongly depends on the type of substituent and is remarkable for derivatives with an electron-withdrawing group, showing reactivity comparable to that of flavinium salts which are the prominent organocatalysts for oxygenations. Because of their high stability and good accessibility, 4-(trifluoromethyl)pyrimidinium and 3,5-dinitropyridinium triflates are the catalysts of choice and were shown to catalyze oxidation of aliphatic and aromatic sulfides to sulfoxides, giving quantitative conversions, high preparative yields and excellent chemoselectivity. The high efficiency of electron-poor heteroarenium salts is rationalized by their ability to readily form adducts with nucleophiles, as documented by low pKR+ values (pKR+ red > -0.5 V). Hydrogen peroxide adducts formed in situ during catalytic oxidation act as substrate oxidizing agents. The Gibbs free energies of oxygen transfer from these heterocyclic hydroperoxides to thioanisole, obtained by calculations at the B3LYP/6-311++g(d,p) level, showed that they are much stronger oxidizing agents than alkyl hydroperoxides and in some cases are almost comparable to derivatives of flavin hydroperoxide acting as oxidizing agents in monooxygenases.
- ?turala, Ji?í,Bohá?ová, Soňa,Chudoba, Josef,Metelková, Radka,Cibulka, Radek
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p. 2676 - 2699
(2015/03/18)
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- Ammonium salt catalyzed oxidation of organosulfides to organosulfoxydes
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The selective oxidation of aromatic and aliphatic organosulfides with H2O2/H2O catalyzed by metal free ammonium salts has been explored. Reactions were performed using 2.5-5 mol % of catalyst loadings, isolating the corres
- Secci, Francesco,Frongia, Angelo,Piras, Pier Paolo
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p. 603 - 605
(2014/01/23)
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- Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine
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An efficient and practical catalytic method for the aerobic oxidative transformation of sulfides into sulfoxides, and thiols into disulfides with formic acid/TEA in the presence of a new, readily available, and stable flavin catalyst 5d is described. This journal is the Partner Organisations 2014.
- Murahashi, Shun-Ichi,Zhang, Dazhi,Iida, Hiroki,Miyawaki, Toshio,Uenaka, Masaaki,Murano, Kenji,Meguro, Kanji
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supporting information
p. 10295 - 10298
(2014/08/18)
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- A molybdenum based metallomicellar catalyst for controlled and selective sulfoxidation reactions in aqueous medium
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A surfactant based molybdenum system that exhibits catalytic activity for sulfoxidation reactions of various organic sulfides in aqueous medium has been developed and comprehensively characterized using IR, XRD, NMR, ESI-MS, DLS and TEM. The catalyst showcases remarkable selectivity for the preparation of both sulfoxides and sulfones in the range of good to excellent yields. Furthermore, the catalyst showed a high degree of tolerance towards various sensitive functional groups such as hydroxyl, acetal, aldehyde, amine, imine, oxime, cyano and alkene. the Partner Organisations 2014.
- Chakravarthy, Rajan Deepan,Ramkumar, Venkatachalam,Chand, Dillip Kumar
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p. 2190 - 2196
(2014/04/17)
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- Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase
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A bacterial flavin-containing monooxygenase (FMO), fused to phosphite dehydrogenase, has been used to explore its biocatalytic potential. The bifunctional biocatalyst could be expressed in high amounts in Escherichia coli and was able to oxidize indole and indole derivatives into a variety of indigo compounds. The monooxygenase also performs the sulfoxidation of a wide range of prochiral sulfides, showing moderate to good enantioselectivities in forming chiral sulfoxides. The Royal Society of Chemistry 2011.
- Rioz-Martinez, Ana,Kopacz, Malgorzata,De Gonzalo, Gonzalo,Torres Pazmino, Daniel E.,Gotor, Vicente,Fraaije, Marco W.
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experimental part
p. 1337 - 1341
(2011/04/23)
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- Transition-metal-free highly efficient aerobic oxidation of sulfides to sulfoxides under mild conditions
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A highly efficient transition-metal-free catalytic system Br 2/NaNO2/H2O has been developed for a robust and economic acid-free aerobic oxidation of sulfides. It is noteworthy that the sulfide function reacts under mild co
- Zhang, Hua,Chen, Chunyu,Liu, Renhua,Xu, Qiang,Zhao, Weiqie
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experimental part
p. 83 - 92
(2010/05/18)
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- NON-NUCLEOTIDE REVERSE TRANSCRIPTASE INHIBITORS
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Compounds of the formula Z: where; A is CH or N; R1 is a substituent to a carbon atom in the ring containing A selected from -S(=O)pRa, where Ra is -C1-C4 alkyl, -ORx, -NRxRx, -NHNRxRx, - NHNHC(=O)ORx, -NRxOH; -C(=O)-Rb, where Rb is -CT-C4-alkyl, ORx, -NRxRx, -NHNRxRx, -NHC1-C3-alkyl-C(=O)Orx -NRxRc, where Rc is H, C1-C4 alkyl, -NRxRx; -C(=0)Rd, -CN, S(=O)pRx where Rd is Rd is C1-C4-alkyl, -ORx, -NRxRx C1-C3-alkyl-O-Cl-C3alkylC(=O)ORx, -C1-C3-alkyl-COORx; -C1-C3alkyl-OH or C1-C4 alkyl ethers or esters thereof (O-Cl-C3alkyl)q-O-Rx a 5 or 6 membered aromatic ring having 1-3 hetero atoms p is 1 or 2; Rx is independently selected from H, C1-C4 alkyl or acetyl; or a pair of Rx can together with the adjacent N atom form a ring; L is -0-, -S(=O),- or -CH2-, where r is 0, 1 or 2; R3-R7 are substituents as defined in the specification; X is -(CR8R8')n-D-(CR8R8')m-; D is a bond, -NR9-, -0-, -S-, -S(=0)- or -S(=0)2-; and pharmaceutically acceptable salts and prodrugs thereof, have utility as HIV antivirals.
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Page/Page column 103-104
(2008/06/13)
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- Synthesis of menthyl sulfinate and sulfoxides on solid phase
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p-Hydroxyphenyl menthyl sulfinate was readily linked to Wang resin. The resulting sulfinate reacted with Grignard reagents and potassium or lithium enolates to give the corresponding sulfoxides or β-ketosulfoxides allowing a study of the chemistry of sulf
- Rolland, Catherine,Hanquet, Gilles,Ducep, Jean-Bernard,Solladié, Guy
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p. 9077 - 9080
(2007/10/03)
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- Synthesis of sulfoxides by the oxidation of sulfides with sodium chlorite catalysed by manganese(III) acetylacetonate in acetone in the presence of alumina
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Systematic oxidations of sulfides with sodium chlorite have been investigated in aprotic solvents under mild and neutral conditions.Metal catalysis is essential for the efficient oxidation, and conversion of a wide variety of diaryl, alkyl aryl, dialkyl and cyclic sulfides into the corresponding sulfoxides can be favoured by the catalytic presence of manganese(III) acetylacetonate in acetone with the aid of moist alumina in general or dry alumina in particular cases in a rapid, high-yielding manner.This simple procedure has also been found to be an easy method for chemoselective transformation of functionalised sulfides without extensive undesirable side-reactions.
- Hirano, Masao,Yakabe, Shigetaka,Clark, James H.,Morimoto, Takashi
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p. 2693 - 2698
(2007/10/03)
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- An Efficient Asymmetric Oxidation of Sulfides to Sulfoxides
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The Sharpless reagent for asymmetric epoxidation was modified by addition of 1 mol equiv of H2O to give a new homogenous reagent (Ti(O-i-Pr)4/diethyl tartrate/H2O/t-BuOOH = 1:2:1:1).This reagent cleanly oxidizes prochiral functionalized sulfides into optically active sulfoxides.The observed ee mainly ranged between 75 and 90percent for alkyl aryl sulfoxides and 50-71percent for dialkyl sulfoxides.A strong temperature dependence on ee was also observed in the asymmetric oxidation of methyl p-tolyl sulfoxide.
- Pitchen, P.,Dunach, E.,Deshmukh, M. N.,Kagan, H. B.
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p. 8188 - 8193
(2007/10/02)
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