- Versatile direct dehydrative approach for diaryliodonium(III) salts in fluoroalcohol media
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We have found that the use of fluoroalcohol media greatly enhanced the efficiency and scope of the direct dehydrative condensation of arenes 1 and hypervalent iodine(iii) compounds; the present clean method has a broad range of applicability as well as un
- Dohi, Toshifumi,Ito, Motoki,Morimoto, Koji,Minamitsuji, Yutaka,Takenaga, Naoko,Kita, Yasuyuki
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- Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts
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Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).
- Soldatova, Natalia S.,Semenov, Artem V.,Geyl, Kirill K.,Baykov, Sergey V.,Shetnev, Anton A.,Konstantinova, Anna S.,Korsakov, Mikhail M.,Yusubov, Mekhman S.,Postnikov, Pavel S.
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supporting information
p. 3566 - 3576
(2021/06/16)
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- N1- and N3-Arylations of Hydantoins Employing Diaryliodonium Salts via Copper(I) Catalysis at Room Temperature
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Copper(I)-catalyzed N-arylation (both N1- and N3-) of hydantoins with diaryliodonium salts as aryl partners at room temperature is reported. The transformation allows diverse scopes on both hydantoins and diaryliodonium salts deliver
- Abha Saikia, Raktim,Barman, Dhiraj,Dutta, Anurag,Jyoti Thakur, Ashim
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supporting information
p. 400 - 410
(2020/12/17)
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- Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts
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A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.
- Bouquin, Maxime,Jaroschik, Florian,Taillefer, Marc
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supporting information
(2021/06/11)
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- Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases
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Equilibrium constants for the associations of 17 diaryliodonium salts Ar2I+X- with 11 different Lewis bases (halide ions, carboxylates, p-nitrophenolate, amines, and tris(p-anisyl)phosphine) have been investigated by titrations followed by photometric or conductometric methods as well as by isothermal titration calorimetry (ITC) in acetonitrile at 20 °C. The resulting set of equilibrium constants KI covers 6 orders of magnitude and can be expressed by the linear free-energy relationship lg KI = sI LAI + LBI, which characterizes iodonium ions by the Lewis acidity parameter LAI, as well as the iodonium-specific affinities of Lewis bases by the Lewis basicity parameter LBI and the susceptibility sI. Least squares minimization with the definition LAI = 0 for Ph2I+ and sI = 1.00 for the benzoate ion provides Lewis acidities LAI for 17 iodonium ions and Lewis basicities LBI and sI for 10 Lewis bases. The lack of a general correlation between the Lewis basicities LBI (with respect to Ar2I+) and LB (with respect to Ar2CH+) indicates that different factors control the thermodynamics of Lewis adduct formation for iodonium ions and carbenium ions. Analysis of temperature-dependent equilibrium measurements as well as ITC experiments reveal a large entropic contribution to the observed Gibbs reaction energies for the Lewis adduct formations from iodonium ions and Lewis bases originating from solvation effects. The kinetics of the benzoate transfer from the bis(4-dimethylamino)-substituted benzhydryl benzoate Ar2CH-OBz to the phenyl(perfluorophenyl)iodonium ion was found to follow a first-order rate law. The first-order rate constant kobs was not affected by the concentration of Ph(C6F5)I+ indicating that the benzoate release from Ar2CH-OBz proceeds via an unassisted SN1-type mechanism followed by interception of the released benzoate ions by Ph(C6F5)I+ ions.
- Legault, Claude Y.,Mayer, Robert J.,Mayr, Herbert,Ofial, Armin R.
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supporting information
(2020/03/13)
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- Practical synthesis of diaryliodonium(iii) triflates using ArI(OAc)2/TfOH/MeCN reaction system
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Diaryliodonium(iii) triflates were synthesized in a safe manner by the reaction of aryliodine(iii) diacetates ArI(OAc)2 with triflic acid (TfOH) in MeCN under mild exothermic conditions. This method provides access to a variety of diaryliodoniu
- Dohi, T.,Kikushima, K.,Kita, Y.,Kobayashi, S.,Komiyama, K.,Shoji, T.
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p. 2328 - 2332
(2020/12/31)
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- Palladium(ii)-catalyzed stereoselective synthesis of: C-glycosides from glycals with diaryliodonium salts
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An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-Aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of
- Das, Mrinmoy,Lee, Jiande,Liu, Xue-Wei,Pal, Kumar Bhaskar
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supporting information
p. 2242 - 2251
(2020/04/07)
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- Catalyst-Free Arylation of Tertiary Phosphines with Diaryliodonium Salts Enabled by Visible Light
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The visible-light-induced arylation of tertiary phosphines with aryl(mesityl)iodonium triflates to produce the quaternary phosphonium salts occurs under mild, metal, and catalyst-free conditions. Photo-excited EDA complexes between diaryliodonium salts an
- Bugaenko, Dmitry I.,Volkov, Alexey A.,Livantsov, Mikhail V.,Yurovskaya, Marina A.,Karchava, Alexander V.
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supporting information
p. 12502 - 12506
(2019/09/16)
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- Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts
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The γ-arylation of substituted silyl-activated butenolides has been studied using a broad scope of unsymmetrical hypervalent diaryliodonium salts via a palladium- or copper-catalysed coupling reaction, yielding interesting reactivity trends. The mild catalytic conditions and coupling partner variability provide access to synthetically useful building blocks toward the pursuit of aryl-lactone containing natural products and allows for facile diversification.
- Alexander, Taylor S.,Clay, Travis J.,Maldonado, Bryan,Nguyen, Johny M.,Martin, David B.C.
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p. 2229 - 2238
(2019/03/06)
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- Regioselective: Ortho -functionalization of bromofluorenecarbaldehydes using TMPMgCl·LiCl
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A highly regioselective functionalization of 7-bromofluorene-2-carbaldehydes, potent organic chromophores, in position C3 using a mild ortho-metallation strategy (DoM) with TMPMgCl·LiCl has been developed. This approach allows the preparation of highly functionalized fluorene derivatives by conversion of the in situ generated metalated species with various electrophiles giving a fast access to novel organic phosphorescent dyes.
- G?bel, Dominik,Clamor, Nils,Nachtsheim, Boris J.
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supporting information
p. 4071 - 4075
(2018/06/12)
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- Glycosyl Cross-Coupling with Diaryliodonium Salts: Access to Aryl C -Glycosides of Biomedical Relevance
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A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis of aryl C-glycosides is reported. This process capitalizes on a stereoretentive reaction of configurationally stable C1 stannanes and is promoted by a palladium catalyst in the presence of a bulky phosphine ligand that suppresses the undesired β-elimination. The utility of this reaction has been demonstrated in the preparation of a series of C-glycosides derived from common saccharides resulting in exclusive transfer of anomeric configuration from the anomeric nucleophile to the product, and in the synthesis of empagliflozin, a commercial antidiabetic drug.
- Yi, Duk,Zhu, Feng,Walczak, Maciej A.
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supporting information
p. 1936 - 1940
(2018/04/12)
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- N-Arylation of DABCO with Diaryliodonium Salts: General Synthesis of N-Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines
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Employing DABCO as a substrate, aryl(mesityl)iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The utility of isolated N-aryl-DABCO salts is demonstrated for the preparation of flibanserin.
- Bugaenko, Dmitry I.,Yurovskaya, Marina A.,Karchava, Alexander V.
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supporting information
p. 6389 - 6393
(2018/10/09)
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- Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides
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Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base and diaryliodonium salt were sufficient to obtain a diverse selection of products within short reaction times. Reactions with thiolactams delivered N-arylated thioamides in good yield at room temperature.
- Villo, Piret,Kervefors, Gabriella,Olofsson, Berit
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supporting information
p. 8810 - 8813
(2018/08/17)
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- A Modular Flow Design for the meta-Selective C?H Arylation of Anilines
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Described herein is an effective and practical modular flow design for the meta-selective C?H arylation of anilines. The design consists of four continuous-flow modules (i.e., diaryliodonium salt synthesis, meta-selective C?H arylation, inline copper extraction, and aniline deprotection) which can be operated either individually or consecutively to provide direct access to meta-arylated anilines. With a total residence time of 1 hour, the desired product could be obtained in high yield and excellent purity without the need for column chromatography, and the residual copper content meets the standards for parenterally administered pharmaceutical substances.
- Gemoets, Hannes P. L.,Laudadio, Gabriele,Verstraete, Kirsten,Hessel, Volker,No?l, Timothy
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supporting information
p. 7161 - 7165
(2017/06/13)
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- Flow Synthesis of Diaryliodonium Triflates
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A safe and scalable synthesis of diaryliodonium triflates was achieved using a practical continuous-flow design. A wide array of electron-rich to electron-deficient arenes could readily be transformed to their respective diaryliodonium salts on a gram scale, with residence times varying from 2 to 60 s (44 examples).
- Laudadio, Gabriele,Gemoets, Hannes P. L.,Hessel, Volker,No?l, Timothy
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p. 11735 - 11741
(2017/11/24)
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- Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone
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A straightforward synthesis of diaryliodonium salts is achieved by using Oxone as the stoichiometric oxidant. Slow addition is the key to obtaining good yields and purities of the reaction products, which are highly useful reagents in many different areas of organic synthesis.
- Soldatova, Natalia,Postnikov, Pavel,Kukurina, Olga,Zhdankin, Viktor V.,Yoshimura, Akira,Wirth, Thomas,Yusubov, Mekhman S.
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- Copper-Catalyzed N-Arylation of Nitroenamines with Diaryliodonium Salts
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A novel synthetic methodology was developed for the N-arylation of nitroenamine derivatives utilizing diaryliodonium triflates and copper(I) chloride as a catalyst. The procedure enables the easy aryl transfer from the hypervalent species under mild catalytic conditions with unusual heteroatom preference and high efficiency.
- Aradi, Klára,Mészáros, ádám,Tóth, Balázs L.,Vincze, Zoltán,Novák, Zoltán
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p. 11752 - 11764
(2017/11/24)
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- P(NMe2)3-promoted ortho-selective arylation of phenols with diaryliodonium triflates via rhodium catalysis
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Rh-catalyzed ortho-selective arylation of free phenol with diaryliodonium triflates to widely existed phenol-containing biaryls have been developed. The use of P(NMe2)3, tBuOLi and CH3CN proved to be critical for the ortho-selectivity of this reaction.
- Liu, Qi-Sheng,Wang, De-Yin,Yang, Jin-Fei,Ma, Zhong-Yi,Ye, Mengchun
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supporting information
p. 3591 - 3595
(2017/06/13)
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- Synthesis of quaternary aryl phosphonium salts: Photoredox-mediated phosphine arylation
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We report a synthesis method for the construction of quaternary aryl phoshonium salts at ambient temperature. The regiospecific reaction involves the coupling of phosphines with aryl radicals derived from diaryliodonium salts under photoredox conditions.
- Fearnley,An,Jackson,Lindovska,Denton
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supporting information
p. 4987 - 4990
(2016/04/08)
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- Metal-free n -arylation of secondary amides at room temperature
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The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.
- Tinnis, Fredrik,Stridfeldt, Elin,Lundberg, Helena,Adolfsson, Hans,Olofsson, Berit
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supporting information
p. 2688 - 2691
(2015/06/16)
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- Well-Defined, Shelf-Stable (NHC)Ag(CF2H) Complexes for Difluoromethylation
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The preparation of the thermally stable, well-defined NHC-ligated difluoromethylated silver complexes 1a,b is described. The complexes were fully characterized, and the structural assignments were ambiguously further confirmed by single-crystal X-ray diffraction. Reactions of [(SIPr)Ag(CF2H)] with a variety of activated electrophiles such as diaryliodonium salts, vinyl(aryl)iodonium salts, aryldiazonium salts, and acid chlorides in the presence or absence of CuI occurred smoothly at room temperature to generate difluoromethylated compounds in good to excellent yields. (Chemical Equation Presented).
- Gu, Yang,Chang, Dalu,Leng, Xuebing,Gu, Yucheng,Shen, Qilong
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supporting information
p. 3065 - 3071
(2015/06/30)
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- Transition-Metal-Free N-Arylation of Pyrazoles with Diaryliodonium Salts
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A new synthetic method was developed for the N-arylation of pyrazoles using diaryliodonium salts. The transformation does not require any transition-metal catalyst and provides the desired N-arylpyrazoles rapidly under mild reaction condition in the presence of aqueous ammonia solution as a mild base without the use of inert atmosphere. The chemoselectivity of unsymmetric diaryliodonium salts was also explored with large number of examples.
- Gonda, Zsombor,Novák, Zoltán
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supporting information
p. 16801 - 16806
(2015/11/16)
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- Copper-catalyzed oxidative ring closure of ortho-cyanoanilides with hypervalent iodonium salts: Arylation-ring closure approach to iminobenzoxazines
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A novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho-cyanoanilides and diaryliodonium triflates via an oxidative arylation-cyclization path. The reaction is supposed to involve the formation of highly active aryl-copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2-dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2-16 h.
- Aradi, Klra,Novk, Zoltn
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supporting information
p. 371 - 376
(2015/03/05)
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- Utilization of Copper-Catalyzed Carboarylation-Ring Closure for the Synthesis of New Oxazoline Derivatives
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A copper-catalyzed carboarylation-ring-closure strategy was used for the modular synthesis of oxazolines via the reaction of 1-aryl- and 1-alkylpropargylamides and diaryliodonium salts. The novel approach enables the efficient, modular synthesis of oxazol
- Sinai, ádám,Vangel, Dóra,Gáti, Tamás,Bombicz, Petra,Novák, Zoltán
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supporting information
p. 4136 - 4139
(2015/09/15)
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- Metal-Free C-Arylation of Nitro Compounds with Diaryliodonium Salts
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An efficient, mild, and metal-free arylation of nitroalkanes with diaryliodonium salts has been developed, giving easy access to tertiary nitro compounds. The reaction proceeds in high yields without the need for excess reagents and can be extended to α-arylation of nitroesters. Nitroalkanes were selectively C-arylated in the presence of other easily arylated functional groups, such as phenols and aliphatic alcohols.
- Dey, Chandan,Lindstedt, Erik,Olofsson, Berit
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supporting information
p. 4554 - 4557
(2015/09/28)
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- Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides
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Pd-mediated C-H bond functionalisation protocols have been designed and developed on tryptophan derivatives and tryptophan-containing peptides. The examination of different arylation reactions (three sets of different conditions A-C), all of which are notable for their low temperatures (≤40°C), allowed identification of unified and complementary synthetic approaches toward a series of functionalised tryptophan-containing products. Tryptophan-containing peptides demonstrated to be susceptible to aromatic oxidation were successfully and selectively modified through the application of diaryliodonium salts in good yields.
- Reay, Alan J.,Williams, Thomas J.,Fairlamb, Ian J. S.
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p. 8298 - 8309
(2015/08/03)
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- Copper-catalyzed oxidative ring closure and carboarylation of 2-ethynylanilides
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A new copper-catalyzed oxidative ring closure of ethynyl anilides with diaryliodonium salts was developed for the highly modular construction of benzoxazines bearing a fully substituted exo double bond. The oxidative transformation includes an unusual 6-exo-dig cyclization step with the formation of C-O and C-C bonds.
- Sinai, Adam,Meszaros, Adam,Gati, Tamas,Kudar, Veronika,Pallo, Anna,Novak, Zoltan
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supporting information
p. 5654 - 5657
(2013/12/04)
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- Arylation with unsymmetrical diaryliodonium salts: A chemoselectivity study
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Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new "anti-ortho effect" has been identified in the arylation of malonates. Several "dummy groups" have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents. Copyright
- Malmgren, Joel,Santoro, Stefano,Jalalian, Nazli,Himo, Fahmi,Olofsson, Berit
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supporting information
p. 10334 - 10342
(2013/09/02)
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- Metal-free arylation of oxygen nucleophiles with diaryliodonium salts
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Phenols and carboxylic acids are efficiently arylated with diaryliodonium salts. The reaction conditions are mild, metal free, and avoid the use of halogenated solvents, additives, and excess reagents. The products are obtained in good-to-excellent yields after short reaction times. Steric hindrance is very well tolerated, both in the nucleophile and diaryliodonium salt. The scope includes ortho- and halo-substituted products, which are difficult to obtain by metal-catalyzed protocols. Many functional groups are tolerated, including carbonyl groups, heteroatoms, and alkenes. Unsymmetric salts can be chemoselectively utilized to obtain products with hitherto unreported levels of steric congestion. The arylation has been extended to sulfonic acids, which can be converted to sulfonate esters by two different approaches. With recent advances in efficient synthetic procedures for diaryliodonium salts the reagents are now inexpensive and readily available. The iodoarene byproduct formed from the iodonium reagent can be recovered quantitatively and used to regenerate the diaryliodonium salt, which improves the atom economy. Copyright
- Jalalian, Nazli,Petersen, Tue B.,Olofsson, Berit
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supporting information
p. 14140 - 14149,10
(2012/12/12)
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- Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts
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A new strategy for the catalytic enantioselective α-arylation of N-acyloxazolidinones with chiral copper(II)-bisoxazoline complexes and diaryliodonium salts is described. The mild catalytic conditions are operationally simple, produce valuable synthetic building blocks in excellent yields and enantioselectivities, and can be applied to the synthesis of important nonsteroidal anti-inflammatory agents and their analogues.
- Bigot, Aurelien,Williamson, Alice E.,Gaunt, Matthew J.
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supporting information; experimental part
p. 13778 - 13781
(2011/10/09)
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- One-pot syntheses of diaryliodonium salts from aryl iodides using peracetic acid as green oxidant
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The rate-accelerating effects of fluoroalcohol solvents for generating trivalent hypervalent iodine species and the conversion into diaryliodonium(iii) salts have been used for the first time to realize a facile and clean one-pot synthesis of diaryliodoni
- Dohi, Toshifumi,Yamaoka, Nobutaka,Itani, Itsuki,Kita, Yasuyuki
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experimental part
p. 529 - 535
(2011/12/15)
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- Synthesis of diaryliodonium triflates using environmentally benign oxidizing agents
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A range of symmetric and unsymmetric diaryliodonium triflates have been prepared employing urea-hydrogen peroxide as the oxidizing agent. The use of aqueous hydrogen peroxide and catalytic systems with methylrhenium trioxide in the oxidation of iodoarenes
- Merritt, Eleanor A.,Malmgren, Joel,Klinke, Felix J.,Olofsson, Berit
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experimental part
p. 2277 - 2280
(2009/12/08)
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- Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions
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We have developed a new site-selective Cu(II)-catalyzed C-H bond functionalization process that can selectively arylate indoles at either the C3 or C2 position under mild conditions. The scope of the arylation process is broad and tolerates broad functionality on both the indole and aryl unit, which makes it amenable to further elaboration. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl species that undergoes initial electrophilic addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group from C3 to C2, and this can be controlled by the nature of the group on the nitrogen atom; free (NH)- and N-alkylindoles deliver the C3-arylated product, whereas N-acetylindoles afford the C2 isomer, both with excellent yield and selectivity. Copyright
- Phipps, Robert J.,Grimster, Neil P.,Gaunt, Matthew J.
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supporting information; experimental part
p. 8172 - 8174
(2009/02/02)
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- Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations
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Symmetrical and unsymmetrical diaryliodonium triflates have been synthesized from both electron-deficient and electron-rich arenes and aryl iodides with mCPBA and triflic acid. A thorough investigation of the optimization, scope and limitations has resulted in an improved one-pot protocol that is fast, high-yielding, and operationally simple. The reaction has been extended to the direct synthesis of symmetrical iodonium salts from iodine and arenes, conveniently circumventing the need for aryl iodides.
- Bielawski, Marcin,Zhu, Mingzhao,Olofsson, Berit
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p. 2610 - 2618
(2008/09/19)
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- Improved preparation of diaryliodonium triflates
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A reagent prepared from a 1:2 molar ratio of (diacetoxy)iodobenzene [PhI(OAc)2] and trifluoromethanesulfonic acid (TfOH) reacts with aromatic compounds to give diaryliodonium triflates in fairly good yields. The high reactivity and high para se
- Kitamura,Matsuyuki,Taniguchi
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p. 147 - 148
(2007/10/02)
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- A convenient preparation of diaryliodonium triflates
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A reagent prepared from iodosylbenzene and trifluoromethanesulfonic acid reacts with aromatic compounds to give diaryliodonium triflates in good yields. A high reactivity of the reagent is also discussed.
- Kitamura,Matsuyuki,Nagata,Furuki,Taniguchi
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p. 945 - 946
(2007/10/02)
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