- Novel preparation and reactivity of poly[4-hydroxy(tosyloxy)iodo]styrenes
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Poly[4-hydroxy(tosyloxy)iodo]styrene (high M.W.) and poly{α-methyl[4-hydroxy(tosyloxy)iodo]styrene} (low M.W.) were prepared from polystyrene (average M.W. = 45,000) and poly(α-methylstyrene) (average M.W. = 6,200), respectively, and their reactivities fo
- Abe,Sakuratani,Togo
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Read Online
- Synthesis method of alpha-carbonyl sulfonate and catalyst used in synthesis method
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The invention provides a nitrogen and carbon co-doped Nb2O5 catalyst for synthesizing alpha carbonyl sulfonate, a preparation method of the nitrogen and carbon co-doped Nb2O5 catalyst, and a synthesizing method of the alpha carbonyl sulfonate by using the catalyst under the driving of visible light. Based on the total weight of the catalyst, the content of nitrogen is 0.01 wt%-1wt%; the content of the carbon is 0.01 wt% to 1.5 wt%. The catalyst provided by the invention is used for preparing alpha-carbonyl sulfonate through olefin aerobic oxidation, the reaction condition is mild, oxygen is used as an oxidant, and other oxidants are not needed. All the raw materials of the catalyst are rich in resource and low in price, and the catalyst can be recycled without inactivation and is very stable to air, water and heat.
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Paragraph 0076-0082; 0086
(2021/04/17)
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- Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles
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A facile and expeditious protocol for the synthesis of 2-arylindole compounds from readily available N-(2-pyridyl)anilines and commercially available α-Cl ketones through iridium-catalyzed C-H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing a straightforward method to obtain structurally diverse and valuable indole scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.
- Cui, Xin-Feng,Qiao, Xin,Wang, He-Song,Huang, Guo-Sheng
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p. 13517 - 13528
(2020/12/15)
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- SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN
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Methods of synthesis of hypervalent iodine reagents and methods for oxidation of organic compounds are disclosed.
- -
-
Paragraph 0178; 0182
(2019/01/15)
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- Continuous-Flow Electrochemical Generator of Hypervalent Iodine Reagents: Synthetic Applications
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An efficient and reliable electrochemical generator of hypervalent iodine reagents has been developed. In the anodic oxidation of iodoarenes to hypervalent iodine reagents under flow conditions, the use of electricity replaces hazardous and costly chemical oxidants. Unstable hypervalent iodine reagents can be prepared easily and coupled with different substrates to achieve oxidative transformations in high yields. The unstable, electrochemically generated reagents can also easily be transformed into classic bench-stable hypervalent iodine reagents through ligand exchange. The combination of electrochemical and flow-chemistry advantages largely improves the ecological footprint of the overall process compared to conventional approaches.
- Elsherbini, Mohamed,Winterson, Bethan,Alharbi, Haifa,Folgueiras-Amador, Ana A.,Génot, Célina,Wirth, Thomas
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supporting information
p. 9811 - 9815
(2019/06/24)
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- Regioselective three-component synthesis of 1,2-diarylindoles from cyclohexanones, α-hydroxyketones and anilines under transition-metal-free conditions
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A facile method for the one-pot synthesis of 1,2-diarylindoles under transition-metal-free conditions is described. Cyclohexanones were used as the aryl sources via the dehydrogenative aromatization process. One C-C and two C-N bonds were selectively formed via a domino reaction. This protocol provides a convenient approach for the construction of valuable bioactive 1,2-diarylindoles from readily available cyclohexanones, α-hydroxyketones and anilines.
- Li, Cheng,Xie, Yanjun,Xiao, Fuhong,Huang, Huawen,Deng, Guo-Jun
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supporting information
p. 4079 - 4082
(2019/04/25)
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- Synthesis, characterisation, and reactivity of novel pseudocyclic hypervalent iodine reagents with heteroaryl carbonyl substituents
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Two new hypervalent iodine reagents containing furan and thiophene moieties in addition to a carbonyl group in the vicinity of the iodine atom were synthesised and characterised. The X-ray analysis of both compounds revealed a strong intramolecular contact between the carbonyl oxygen and the hypervalent iodine atom with tosylate as a counter ion. The two reagents showed a broad range of synthetic applications and proved to be versatile oxidizing agents.
- Qurban, Jihan,Elsherbini, Mohamed,Alharbi, Haifa,Wirth, Thomas
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supporting information
p. 7998 - 8000
(2019/07/12)
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- Oxidase catalysis via aerobically generated hypervalent iodine intermediates
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The development of sustainable oxidation chemistry demands strategies to harness O'2 as a terminal oxidant. Oxidase catalysis, in which O'2 serves as a chemical oxidant without necessitating incorporation of oxygen into reaction products, would allow diverse substrate functionalization chemistry to be coupled to O'2 reduction. Direct O'2 utilization suffers from intrinsic challenges imposed by the triplet ground state of O'2 and the disparate electron inventories of four-electron O'2 reduction and two-electron substrate oxidation. Here, we generate hypervalent iodine reagents - a broadly useful class of selective two-electron oxidants - from O'2. This is achieved by intercepting reactive intermediates of aldehyde autoxidation to aerobically generate hypervalent iodine reagents for a broad array of substrate oxidation reactions. The use of aryl iodides as mediators of aerobic oxidation underpins an oxidase catalysis platform that couples substrate oxidation directly to O'2 reduction. We anticipate that aerobically generated hypervalent iodine reagents will expand the scope of aerobic oxidation chemistry in chemical synthesis.
- Maity, Asim,Hyun, Sung-Min,Powers, David C.
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p. 200 - 204
(2018/02/06)
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- A DEVELOPING AGENT PRECURSOR FOR LASER MARKABLE COMPOSITIONS
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The invention relates to novel laser markable compositions comprising developing agent precursors according to formula (I).
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Paragraph 0141
(2019/01/07)
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- Facile synthesis of polysubstituted cyclopropanes using α-tosyloxyketones
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A facile synthesis of polysubstituted cyclopropanes (5) by the treatment of pyridinium ylides, generated in situ from pyridinium toslyates (2), with arylidenemalonitrile (4) is presented. Pyridinium toslyates (2) were obtained by reacting α-tosyloxyketone
- Rana, Neena,Nain, Sonia,Kumar, Dinesh,Kumar, Ravi
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p. 505 - 507
(2018/02/09)
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- Metal-free C(sp3)-H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones
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Pyridin-2-ylmethyl tosylate derivatives are obtained in high yields from 2-alkylpyridine 1-oxides via a [3,3]-sigmatropic rearrangement of the adduct between 2-alkylpridine 1-oxides with benzenesulfonyl chlorides. Moreover, alkylnitrones also undergo [3,3]-sigmatropic rearrangement to give α-tosylated ketones after hydrolysis. Substitution reactions with nucleophiles then lead to diverse useful functionalizations for the synthesis of pincer ligands.
- Wang, Chang-Sheng,Dixneuf, Pierre H.,Soulé, Jean-Fran?ois
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p. 4954 - 4957
(2018/07/25)
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- Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts
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A practical method for the asymmetric transfer hydrogenation of α-substituted ketones was developed utilizing oxo-tethered N-sulfonyldiamine-ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2-bromoacetophenone (98%) and 2-chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation under the typical reaction conditions using an azeotropic 5:2 mixture of HCO2H and Et3N. A range of functional groups, such as halogens, methoxy, nitro, dimethylamino, and ester groups, were well tolerated, highlighting the potential of this method. Nearly complete selectivity with a preferable ee was maintained even with a substrate/catalyst (S/C) ratio of 5000. This catalyst system was also effective for the asymmetric reduction of α-sulfonated ketones without eroding the leaving group. (Figure presented.).
- Yuki, Yamato,Touge, Taichiro,Nara, Hideki,Matsumura, Kazuhiko,Fujiwhara, Mitsuhiko,Kayaki, Yoshihito,Ikariya, Takao
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supporting information
p. 568 - 574
(2017/12/13)
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- Synthesis of α-sulfonyloxyketones via iodobenzene diacetate (PIDA)-mediated oxysulfonyloxylation of alkynes with sulfonic acids
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A simple yet powerful method to synthesize a variety of α-sulfonyloxyketones has been developed. This novel method can be applied for the direct oxysulfonyloxylation of alkynes with sulfonic acids to access a variety of α-sulfonyloxyketones. Compared to the reported methods for the application of PIDA, this study expands its application scope and uses it not only as the oxidant but also as the carrier of O to form the carbonyl group in the products. In addition, under the established conditions, this methodology not only exhibits a broad substrate scope but also demonstrates exclusive regioselectivity with substrates of 1,2-disubstituted internal alkynes.
- Zhang, Yang,Tan, Hua,Liu, Weibing
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p. 54017 - 54020
(2017/12/05)
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- PhI(OAc)2-promoted umpolung acetoxylation of enamides for the synthesis of α-acetoxy ketones
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Umpolung is a fundamental concept in organic chemistry, which provides an alternative strategy for the synthesis of target compounds which were not easily accessible by conventional methods. Herein, a mild and efficient PhI(OAc)2-promoted umpolung acetoxylation reactions of enamides was developed for the synthesis of α-acetoxy ketones. The reaction tolerates a wide range of functional groups and affords α-acetoxy ketones in good to excellent yields. PhI(OAc)2 serves as a source of acetoxy in the reaction.
- Chen, Ming,Zhang, Wei,Ren, Zhi-Hui,Gao, Wen-Yun,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 761 - 768
(2017/06/05)
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- Enolonium Species—Umpoled Enolates
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Enolonium species/iodo(III)enolates of carbonyl compounds have been suggested to be intermediates in a wide variety of hypervalent iodine induced chemical transformations of ketones, including α-C?O, α-C?N, α-C?C, and α-carbon–halide bond formation, but they have never been characterized. We report that these elusive umpoled enolates may be made as discrete species that are stable for several minutes at ?78 °C, and report the first spectroscopic identification of such species. It is shown that enolonium species are direct intermediates in C?O, C?N, C?Cl, and C?C bond forming reactions. Our results open up chemical space for designing a variety of new transformations. We showcase the ability of enolonium species to react with prenyl, crotyl, cinnamyl, and allyl silanes with absolute regioselectivity in up to 92 % yield.
- Arava, Shlomy,Kumar, Jayprakash N.,Maksymenko, Shimon,Iron, Mark A.,Parida, Keshaba N.,Fristrup, Peter,Szpilman, Alex M.
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supporting information
p. 2599 - 2603
(2017/02/26)
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- Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles
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New pseudocyclic benziodoxole tosylates were prepared by the treatment of 1-hydroxybenziodoxolones with p-toluenesulfonic acid or via ligand transfer reaction between PhI(OH)OTs (Koser's reagent) and substituted 2-iodobenzoic acids under mild condition. S
- Yoshimura, Akira,Klasen, Scott C.,Shea, Michael T.,Nguyen, Khiem C.,Rohde, Gregory T.,Saito, Akio,Postnikov, Pavel S.,Yusubov, Mekhman S.,Nemykin, Victor N.,Zhdankin, Viktor V.
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supporting information
p. 691 - 695
(2017/01/18)
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- Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations
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A series of rate studies were conducted to evaluate the steric and electronic properties that govern the reactivity of iodoarene amide catalysts in the α-oxytosylation of propiophenone. A meta-substituted benzamide catalyst emerged as the most reactive. This catalyst was employed in the α-oxytosylation of a series of substituted propiophenones, returning the α-tosyloxy ketone products in excellent isolated yield.
- Lex, Timothy R.,Swasy, Maria I.,Whitehead, Daniel C.
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p. 12234 - 12243
(2016/01/09)
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- General Method for the Preparation of Electron-Deficient Imidazo[1,2-a]pyridines and Related Heterocycles
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A new annulation method for the preparation of the imidazo[1,2-a]pyridine ring system under mild conditions is presented. Treatment of a 2-aminopyridine with a dimethylketal tosylate in acetonitrile at elevated temperature (80-140°C) in the presence of catalytic Sc(OTf)3 provides the imidazo[1,2-a]pyridine product in good yield. The annulation method is broadly applicable to electron-poor 2-aminopyridines and displays a complementary profile to the classic preparation of the imidazo[1,2-a]pyridine ring system by reaction of a bromoketone with electron-rich and -neutral substrates. The scope of the process and mechanistic considerations are discussed.
- McDonald, Ivar M.,Peese, Kevin M.
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supporting information
p. 6002 - 6005
(2016/01/09)
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- A convenient [hydroxy(tosyloxy)iodo]benzene-mediated one-pot synthesis of 2-arylimidazo[2,1-b[benzothiazoles
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Several 2-arylimidazo[2,1-b]benzothiazoles (4) have been conveniently synthesized in one-pot reactions via α-tosyloxylation of enolizable ketones (1) using [hydroxy(tosyloxy)iodo]benzene 2 in acetonitrile, followed by treatment with 2-amino-6-(substituted
- Sumran, Garima,Aggarwal, Ranjana
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p. 170 - 177
(2015/10/20)
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- Novel α-tosyloxylation of ketones catalyzed by the in situ generated hypoiodous acid from alkyl iodide
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Using a catalytic amount of 1-iodopropane, a novel and efficient procedure has been developed for direct preparation of α-tosyloxyketones from ketones. In this protocol, 1-iodopropane is first oxidized into iodosylpropane, which decomposes to form the key
- Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
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p. 5851 - 5854
(2015/01/16)
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- 2,4,6-Tris(4-iodophenoxy)-1,3,5-triazine as a new recyclable "iodoarene" for in situ generation of hypervalent iodine(III) reagent for α-tosyloxylation of enolizable ketones
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The synthesis of 2,4,6-tris[(4-iodo)phenoxy)]-1,3,5-triazine 6, as a new recyclable nonpolymeric analogue of iodobenzene is achieved using the reaction of 2,4,6-trichloro-1,3,5-triazine with 4-iodophenol in the presence of KOH. The application of 6 as a r
- Thorat, Prerana B.,Bhong, Bhagyashree Y.,Shelke, Amol V.,Karade, Nandkishor N.
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p. 3332 - 3335
(2014/06/09)
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- Oxidative breakdown of iodoalkanes to catalytically active iodine species: A case study in the α-tosyloxylation of ketones
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Catalysis of the oxidative processes by iodoarenes has become a promising direction in synthesis. The mechanism, involving the well-known isolable hypervalent iodine species, is generally limited to aromatic iodides, since the corresponding aliphatic spec
- Guo, Wusheng,Vallcorba, Oriol,Vallribera, Adelina,Shafir, Alexandr,Pleixats, Roser,Rius, Jordi
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p. 468 - 472
(2014/03/21)
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- Effective α-tosyloxylation of ketones using 1,1,1-trifluoro-2-iodoethane as catalyst
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With 1,1,1-trifluoro-2-iodoethane as catalyst, a novel and efficient procedure has been developed for preparation of α-tosyloxyketones from ketones. In this protocol, 1,1,1-trifluoro-2-iodoethane is first oxidized by m-chloroperbenzoic acid to a hypervale
- Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
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supporting information
p. 3264 - 3270
(2015/10/06)
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- Iodine-mediated α-sulfonyloxylation of alkyl aryl ketones with oxone and sulfonic acids
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Alkyl aryl ketones are converted into the corresponding α-sulfonyloxyketones, in moderate to excellent yields, via a novel procedure that utilizes Oxone, p-toluenesulfonic acid or methanesulfonic acid and molecular iodine in a mixture of aceton
- Kikui, Hiroki,Moriyama, Katsuhiko,Togo, Hideo
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p. 791 - 797
(2013/04/10)
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- Sol-gel immobilized aryl iodides for the catalytic oxidative α-tosyloxylation of ketones
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New hybrid silica materials M1-M4, derived from mono and bis-silylated aryl iodides, have been prepared via sol-gel processes, either by the hydrolytic polycondensation of a bis-silylated monomer or by the co-gelification of a monosilylated precursor with
- Guo, Wusheng,Monge-Marcet, Amàlia,Catto?n, Xavier,Shafir, Alexandr,Pleixats, Roser
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p. 192 - 199
(2013/02/25)
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- An iodobenzene-catalysed domino route toward quinoxaline derivatives from simple ketones and o-phenylenediamines in one pot
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An iodobenzene-catalysed domino route to quinoxalines from ketones and o-phenylenediamines in one pot has been developed. This transformation consisted of the generation of Koser's generation, α-tosyloxylation of ketones, nucleophilic substitution and intramolecular dehydration with o-phenylenediamines, and dehydrogenation. Website
- Li, Xiaoqing,Zhou, Can,Hu, Zhiyan,Xu, Xiangsheng
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p. 579 - 581
(2013/10/22)
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- Modified one-pot multicomponent diastereoselective synthesis of trans-2,3-Dihydrofuro[3,2-c]coumarins via in situ-generated α- tosyloxyketones
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A modified protocol for diastereoselective synthesis of differently substituted trans-2,3-dihydrofuro[3,2-c]coumarins is developed via, a one-pot multicomoponent reaction starting from aromatic aldehydes, 4-hydroxycoumarin, and α-tosyloxyacetophenones wit
- Kumar, Ravi,Wadhwa, Deepak,Hussain, Khalid,Prakash, Om
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p. 1802 - 1807
(2013/05/22)
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- A novel one-pot method for αα-tosyloxylation of ketones using a catalytic amount of ammonium iodide
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A novel one-pot procedure was designed for the preparation of various α-tosyloxy ketones in good yields by the reaction of ketones with m-chloroperoxybenzoic acid and p-toluenesulfonic acid monohydrate in the presence of catalytic amounts of ammonium iodi
- Hu, Jiantao,Zhu, Min,Xu, Yuan,Yan, Jie
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experimental part
p. 1226 - 1232
(2012/05/20)
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- Synthesis of highly substituted oxazoles through iodine(III)-mediated reactions of ketones with nitriles
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In the presence of trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethanesulfonyl) imide (Tf2NH), iodosobenzene (PhI=O) efficiently promoted the reactions of dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions.
- Saito, Akio,Hyodo, Nao,Hanzawa, Yuji
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supporting information
p. 11046 - 11055
(2012/11/07)
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- Iodoarene-mediated α-tosyloxylation of ketones with MCPBA and p-toluenesulfonic acid
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Alkyl aryl ketones and dialkyl ketones could be converted into the corresponding α-tosyloxy ketones by the reaction with MCPBA and p-toluenesulfonic acid monohydrate (PTSA ? H2O) in the presence of a catalytic amount of molecular iodine (I
- Tanaka, Ayumi,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 1853 - 1858
(2011/09/16)
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- Catalytic, asymmetric, interrupted Feist-Benary reactions of α-tosyloxyacetophenones
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A new variant of the Interrupted Feist-Benary (IFB) reaction uses α-tosyloxyacetophenones as electrophiles and proceeds in good yields and excellent enantioselectivities.
- Calter, Michael A.,Korotkov, Alexander
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supporting information; experimental part
p. 6328 - 6330
(2012/01/11)
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- Novel preparation of polymer-supported iodobenzene and its synthetic utility as a recyclable reagent with m-chloroperbenzoic acid
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Three novel polymer-supported iodobenzene compounds A0, A 6, and A10 were prepared from the reaction of commercially available cross-linked poly(p-chloromethyl)styrene with m-iodobenzylalcohol, 6-(m-iodobenzyloxy)-1-hexanol, and 10-(m-iodobenzyloxy)-1-decanol. Their catalytic reactivity and reusability for the oxidative α-tosyloxylation of ketones and the cyclization of N-methoxy-2-arylethanesulfonamides in the presence of m-chloroperbenzoic acid (mCPBA) were confirmed to provide -tosyloxyketones and N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides, respectively, in good yields. Georg Thieme Verlag Stuttgart · New York.
- Suzuki, Yuhsuku,Togo, Hideo
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experimental part
p. 2355 - 2360
(2010/09/18)
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- Iodobenzene-catalyzed synthesis of α-azidoketones and α-thiocyanatoketones from aryl ketones with MCPBA as a cooxidant
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Iodobenzene-catalyzed synthesis of α-azidoketones and α-thiocyanatoketones from aryl ketones with MCPBA as a cooxidant is described. The method is simple, rapid and practical, generating α-azidoketones and α-thiocyanatoketones from the aryl ketone without
- Chang, Ya-Li,Chung, Chi-Lin,Wu, Fang-Wen,Wang, Huey-Min,Hou, Rei-Sheu,Kang, Iou-Jiun,Chen, Ling-Ching
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experimental part
p. 149 - 152
(2011/04/16)
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- Iodobenzene-catalyzed synthesis of imidazo[1,2-a]pyridines from aryl ketones with mCPBA in ionic liquid
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Iodobenzene-catalyzed synthesis of imidazo[1,2-a]pyridines from aryl ketones with mCPBA as a cooxidant in ionic liquid is described. The method is simple, rapid and practical, generating Imidazo[1,2-a]pyridines from the aryl ketone without isolation of α-
- Chang, Ya-Li,Wang, Huey-Min,Hou, Rei-Sheu,Kang, Iou-Jiun,Chen, Ling-Ching
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experimental part
p. 153 - 156
(2011/04/16)
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- Development of new recyclable reagents and catalytic systems based on hypervalent iodine compounds
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Recent advances in the development of polymer-supported iodine(V) oxidants, recyclable monomeric hypervalent iodine(III) reagents and catalytic systems based on hypervalent iodine compounds are discussed. These efficient and environmentally friendly reagents and catalysts are particularly useful for oxidative transformations of alcohols to carbonyl compounds and for oxidations at the benzylic position.
- Yusubov, Mekhman S.,Zhdankin, Viktor V.
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p. 185 - 191
(2011/03/19)
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- α-Tosyloxylation of ketones with ion-supported[hydroxy(tosyloxy)iodo] benzene
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A new room-temperature ionic liquid (RTIL) supported [hydroxy(tosyloxy) iodo]benzene (ion-supported HTIB) reagent was synthesised by three kinds of effective methods in high yields, which combined the advantages of ionic liquids and the hypervalent iodine
- Su, Feng,Zhang, Jizhen,Jin, Guangyu,Qiu, Tao,Zhao, Dejian,Jia, Hongbin
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experimental part
p. 741 - 744
(2010/03/24)
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- M-iodosylbenzoic acid: Recyclable hypervalent iodine reagent for-tosyloxylation and-mesyloxylation of ketones
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m-Iodosylbenzoic acid-mediated reactions of various carbonyl compounds provided-organosulfonyloxy carbonyl compounds in good yields. The final products could be easily isolated without any chromatographic purification by simple treatment of the crude mixt
- Yusubov, Mekhman S.,Funk, Tatyana V.,Yusubova, Roza Y.,Zholobova, Galina,Kirschning, Andreas,Park, Joo Yeon,Chi, Ki-Whan
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experimental part
p. 3772 - 3784
(2009/12/06)
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- 4-MeC6H4I-mediated efficient -tosyloxylation of ketones with oxone and p- toluenesulfonic acid in acetonitrile
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Various alkyl aryl ketones, dialkyl ketones, and cycloheptanone were efficiently converted into the corresponding -tosyl-oxy ketones in good yields by using Oxone and p-toluenesulfonic acid monohydrate in the presence of p-iodotoluene in aceton
- Tanaka, Ayumi,Togo, Hideo
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experimental part
p. 3360 - 3364
(2010/03/03)
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- Iodoxolone-based hypervalent iodine reagents
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Image Persented The fast access to simple (Z)-3-iodo acrylic acid derivatives which can be easily oxidized to the corresponding hypervalent iodine(III) reagents is described. They can be used for various reactions with superior or similar reactivity as conventional hypervalent iodine(III) reagents.
- Shah, Azhar-Ul-Haq A.,Khan, Zulfiqar A.,Choudhary, Naila,Lohoelter, Christine,Schaefer, Sascha,Marie, Guillaume P.L.,Farooq, Umar,Witulski, Bernhard,Wirth, Thomas
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supporting information; experimental part
p. 3578 - 3581
(2011/02/22)
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- Convenient synthesis of symmetrical diketosulfides from enolizable ketones using [hydroxy(tosyloxy)iodo]benzene and Na2S·9H20
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An efficient method for the preparation of symmetrical diketosulfides of the type ArCOCH2SCH2COAr has been developed from the reaction of [hydroxy(tosyloxy)iodo]benzene with various acetophenones, followed by treatment with Na2
- Karade, Nandkishor N.,Tiwari, Girdharilal B.,Gampawar, Sumit V.,Shinde, Sandeep V.
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experimental part
p. 172 - 176
(2009/09/30)
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- Synthesis of 2,5-disubstituted 1,3,4-oxadiazine and 1,3,4-thiadiazine from substituted acetophenones and acid hydrazides using [Hydroxyl(tosyloxy)iodo] benzene
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A novel and direct method for the efficient synthesis of 2,5-disubstituted 1,3,4-oxadiazines from the reactions of [hydroxy(tosyloxy)iodo]benzene with substituted acetophenones, followed by the treatment with acid hydrazide and K2CO3, is reported. The met
- Karade, Nandkishor N.,Kondre, Jeevan M.,Gampawar, Sumeet V.,Shinde, Sandeep V.
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experimental part
p. 2279 - 2287
(2009/12/03)
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- Enantioselective synthesis of 1-arylethanediols by rhodium-catalyzed transfer hydrogenation of α-tosyloxyarylketones
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Catalytic transfer hydrogenation of α-tosyloxyarylketones mediated by a chiral rhodium complex using an azeotropic mixture of formic acid/triethylamine afforded the corresponding 1-arylethanediol monotosylates in excellent yield with high enantioselectivity.
- Lee, Do-Min,Kumaraswamy, Gullapalli,Lee, Kee-In
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experimental part
p. 73 - 78
(2010/03/26)
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- One-Pot Protocol for Synthesis of -Organosulfonyloxy Ketones from Secondary Alcohols Using Hypervalent Iodine(V)-Mediated Oxidations
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Tosyloxy ketones and -mesyloxy ketones were directly prepared from alcohols in one pot by treatment with hypervalent iodine(V) reagents in combination with p-toluenesulfonic acid and methanesulfonic acid, respectively, in moderate to good yields. Reaction
- Deshmukh, Swapnil S.,Huddar, Sameerana N.,Akamanchi, Krishnacharya G.
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experimental part
p. 3101 - 3110
(2009/11/30)
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- A new application of hypervalent iodine (λ5) reagents with organosulfonic acids for direct α-organosulfonyloxylation carbonyl compounds
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Hypervalent iodine (λ5) reagents in combination with p-toluenesulfonic acid when reacted with ketones under reflux temperature in acetonitrile gave α-tosyloxy ketones in moderate to excellent yields. The reaction was developed further for both
- Mahajan, Ulhas S.,Akamanchi, Krishnacharya G.
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experimental part
p. 987 - 990
(2009/04/04)
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- Direct α-oxytosylation of ketones by using pentavalent organobismuth reagents
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A new method for the preparation of α-tosyloxy ketones by a direct oxytosylation of ketones using a combination of heterocyclic pentavalent organobismuth compounds and p-toluenesulfonic acid monohydrate is described. Copyright
- Sakurai, Naoto,Mukaiyama, Teruaki
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p. 388 - 389
(2008/09/20)
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- One-pot synthesis of α-formyloxy ketones from enolizable ketones
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One-pot synthesis of α-formyloxy tones as well as α-acetoxy ketones from enolizable ketones and [hydroxy(tosyloxy) iodo] benzene (HTIB)/polymer supported [hydroxy(tosyloxy) iodo] benzene (PSHTIB) in N,N-dimethylformamide (DMF)/N, N-dimethylacetamide (DMA)
- Kumar, Sunil,Kumar, Ashok,Gupta, Rakesh K.,Kumar, Devinder
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p. 338 - 345
(2008/04/01)
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- Solvent-free synthesis of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one from Dess-Martin periodinane and its synthetic utility for α-tosyloxylation of ketones
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The solvent-free synthesis of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one is reported from Dess-Martin periodinane and p-toluenesulfonic acid monohydrate using a grinding technique and is subsequently utilized for the α-tosyloxylation of a range of enolisable ketones.
- Karade, Nandkishor N.,Tiwari, Girdharilal B.,Shinde, Sandeep V.,Gampawar, Sumeet V.,Kondre, Jeevan M.
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p. 3441 - 3443
(2008/09/21)
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- Preparation and X-ray structures of 3-[bis(trifluoroacetoxy)iodo]benzoic acid and 3-[hydroxy(tosyloxy)iodo]benzoic acid: New recyclable hypervalent iodine reagents
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(Chemical Equation Presented) Preparation, structural characterization, and reactivity of 3-[bis(trifluoroacetoxy)iodo]benzoic acid and 3-[hydroxy-(tosyloxy)iodo]benzoic acid, new recyclable iodine(III) reagents derived from 3-iodosylbenzoic acid, are described. The reduced form of these reagents, 3-iodobenzoic acid, can be easily recovered from the reaction mixtures using ion-exchange resin or basic aqueous workup followed by acidification with HCl.
- Yusubov, Mekhman S.,Funk, Tatyana V.,Chi, Ki-Whan,Cha, Eun-Hye,Ghyung, Hwa Kim,Kirschning, Andreas,Zhdankin, Viktor V.
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p. 295 - 297
(2008/09/17)
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- PhI- and polymer-supported PhI-catalyzed oxidative conversion of ketones and alcohols to α-tosyloxyketones with m-chloroperbenzoic acid and p-toluenesulfonic acid
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Various ketones were converted to the corresponding α-tosyloxyketones with mCPBA and p-toluenesulfonic acid in the presence of a catalytic amount of iodobenzene. Moreover, secondary alcohols were directly converted to the corresponding α-tosyloxyketones using mCPBA and catalytic amounts of iodobenzene and potassium bromide, followed by treatment with p-toluenesulfonic acid in a one-pot manner. Poly(4-iodostyrene) could be also used as a recyclable catalyst for the same α-tosyloxylation of ketone.
- Yamamoto, Yukiharu,Kawano, Yuhta,Toy, Patrick H.,Togo, Hideo
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p. 4680 - 4687
(2007/10/03)
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- Efficient conversion of ketones to α-tosyloxyketones with m-chloroperbenzoic acid and p-toluenesulfonic acid in the presence of catalytic amount of IL-supported PhI in [emim]OTs
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Various ketones were smoothly converted into the corresponding α-tosyloxyketones with MCPBA and p-toluenesulfonic acid in the presence of a catalytic amount of ionic-liquid (IL)-supported PhI in room temperature ionic liquid, [emim]OTs. Moreover, the pres
- Akiike, Junnosuke,Yamamoto, Yukiharu,Togo, Hideo
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p. 2168 - 2172
(2008/02/10)
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- Direct α-oxytosylation of carbonyl compounds: One-pot synthesis of heterocycles
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N-Methyl-O-tosylhydroxylamine is an effective reagent for the direct α-oxytosylation of carbonyl compounds. The reactions proceed smoothly at room temperature in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsymmetrical substrates regioselectivity for primary over secondary centers is observed and complete regiospecificity for primary over tertiary centers is obtained. Addition of a bis-heteronucleophile directly to the crude reaction mixture in a one-pot process leads to the corresponding heterocyclic product.
- John, Oliver R. S.,Killeen, Niall M.,Knowles, Deborah A.,Yau, Sze Chak,Bagley, Mark C.,Tomkinson, Nicholas C. O.
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p. 4009 - 4012
(2008/02/11)
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