Patent

特許第5328745 号 リチウム２次電池				  
特許第5680509 号 メソイオン化合物を含む電池用電解液，及び当該電解液を含む電池
特許第5718867 号 リチウム電池用電解液及びその製造方法，並びに当該リチウム電池用電解液を備えるリチウム電池					 
特許第5827334 号 電池用電解液及びその製造方法，並びに当該電解液を備える電池
特許第5830047 号 マグネシウム電池用電解液，及び当該電解液を含むマグネシウム電池

Paper

(122) Synthesis, Structural Characterization, and Reactions of an Adduct Formed between Mesoionic 1,3-diphenyltetrazolium-5-thiolate and Diiodine
Yuta Matsukawa, Mirai Nakata,Tsunehisa Hirashita, and Shuki Araki
Tetrahedron Letters, in press.

(121) Synthesis of stable class 5 mesoionic benzo[c]tetrazolo[2,3-a]cinnolinium thiolate, dicyanomethylide, and amides
Mirai Nakata,Tsunehisa Hirashita, Yoshikazu Konishi and Shuki Araki
Organic & Biomolecular Chemistry, (2023), 21, 4282-4289.

(120) Palladium-Catalyzed Selective o-Bromination of Mesoionic 1,3- Diphenyltetrazolium-5-olate: Switching the Directing Group from Nitrogen to Oxygen
Tsunehisa Hirashita, Harue Watanabe, Yuki Harada, Hideaki Kurabayashi, Yukinobu, Yamashita, Shiyogo Oizumi, Shuki Araki
ChemistrySelect, (2021), 6, 13414-13418.

(119) Preparative Synthesis of 1,3-Dialkyltetrazolium-5-thiolates from 1-Alkyltetrazole-5- thiols
Tsunehisa Hirashita, Suguru Murakami, Takuo Shoji, Hideaki Kurabayashi, Shuki Araki
Bulletin of the Chemical Society of Japan, (2021), 94, 2956-2961.

(118) The Mizoroki-Heck Reaction in Mesoionic 1-Butyl-3-methyltetrazolium-5-olate
Hideaki Kurabayashi, Tsunehisa Hirashita, Shuki Araki
Tetrahedron, 2021, 99, 132450.

(117) Reactions between 5-Nitroso-1,3-diphenyltetrazolium Salts and Electron-rich Arenes, Amines, Thiophenol, Sulfoxides, and Thioanisole
Matsukawa, Yuta; Hirashita, Tsunehisa; Araki, Shuki
Bulletin of the Chemical Society of Japan, 2019, 92, 540-544.

(116) Copper(I)- and Mesoionic-Hydroxyamide-Catalyzed Chemoselective Aerobic Oxidation of Primary Benzylic Alcohols
Matsukawa, Yuta; Hirashita, Tsunehisa
Synlett, 2019, 30, 315-318.

(115) Revisiting Sodium Hypochlorite Pentahydrate (NaOCl-5H2O) for the Oxidation of Alcohols in Acetonitrile without Nitroxyl Radicals
Hirashita, Tsunehisa; Sugihara, Yuto; Ishikawa, Shota; Naito, Yohei; Matsukawa, Yuta; Araki, Shuki
Synlett, (2018), 29, 2404–2407.

(114) Indium-Mediated Allylation of Carbonyl Compounds in Ionic Liquids: Effect of Salts in Ionic Liquids
Hirashita, Tsunehisa; Takahashi, Fusako; Noda, Takayuki; Takagi, Yuji; Araki, Shuki
Molecules, (2018), 1695−1703.

(113) Nitrosotetrazolium-Catalyzed Aerobic Oxidation of Alcohols to the Corresponding Carbonyl Compounds
Matsukawa, Yuta; Hirashita, Tsunehisa; Araki, Shuki
European Journal of Organic Chemistry, (2018), 1359−1363.

(112) 5-Nitroso-1,3-diphenyltetrazolium Salt as a Mediator for the Oxidation of Alcohols
Matsukawa, Yuta; Hirashita, Tsunehisa, Araki, Shuki
Tetrahedron (2017), 73, 6052–6056.

(111) Ionic TEMPO in Ionic Liquids: Specific Promotion of the Aerobic Oxidation of Alcohols
Hirashita, Tsunehisa, Nakanishi, Makoto, Uchida, Tomoya, Yamamoto, Masakazu, Arak,i Shuki, Arends, Isabel W. C. E., Sheldon, Roger A.
ChemCatChem (2016), 8, 2704–2709.

(110) Analysis of Pigments in the Printing Inks of the First Japanese Postage Stamps, the Hand-Engraved Issues
Araki, Shuki; Kondo, Emi; Shibata, Tomohiro; Yokota,Takeshi; Marena, Suzuki, Hirashita, Tsunehisa Yamaguchi, Koichi; Matsumoto, Hirok; Murase, Yoshiaki.
Bulletin of the Chemical Society of Japan, (2016), 89, 595–602.

(109) Condensation of indoles and aldehydes in subcritical water without the addition of catalysts
Hirashita, Tsunehisa; Ogawa, Masaki; Hattori, Reina; Okochi, Sota; Araki, Shuki.
Bulletin of the Chemical Society of Japan, (2015), 88, 1760-1764.

(108) Nickel-catalyzed indium(I)-mediated syn-selective propargylation of aldehydes
Hirashita, Tsunehisa; Suzuki, Yuuki; Tsuji, Hiromitsu; Sato, Yoshiki; Naito, Kojiro; Araki, Shuki.
European Journal of Organic Chemistry, (2012), 5668-5672.

(107) Ionic liquid-accelerated allylation of carbonyl compounds with a catalytic amount of indium generated from in situ reduction of InCl₃ with aluminium
Hirashita, Tsunehisa; Sato, Yuki; Yamada, Dai; Takahashi, Fusako; Araki, Shuki.
Chemistry Letters, (2011), 40, 506-507.

(106) Direct benzylation and allylic alkylation in high-temperature water without added catalysts
Hirashita, Tsunehisa; Kuwahara, Sho; Okochi, Sota; Tsuji, Makoto; Araki, Shuki.
Tetrahedron Letters (2010), 51, 1847-1851.

(105) Cyclopropanation of Electron-Deficient Alkenes with Activated Dibromomethylene Compounds Mediated by Lithium Iodide or Tetrabutylammonium Salts
Kawai, Daisuke; Kawasumi, Katsuaki; Miyahara, Tsukasa; Hirashita, Tsunehisa; Araki, Shuki.
Tetrahedron (2009), 65, 10390-10394.

(104) Mesoionic carbenes: Reactions of 1,3-diphenyltetrazol-5-ylidene with electron-deficient alkenes, and synthesis and catalytic activities of the (tetrazol-5-ylidene)rhodium(I) complexes.
Araki, Shuki; Yokoi, Keisaku; Sato, Ryosuke; Hirashita, Tsunehisa; Setsune, Jun-Ichiro.
Journal of Heterocyclic Chemistry (2009), 46, 164-171.

(103) Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides.
Araki, Shuki; Hirose, Satoshi; Konishi, Yoshikazu; Nogura, Masatoshi; Hirashita, Tsunehisa.
Beilstein Journal of Organic Chemistry (2009), No. 8.

(102) Cyclopropanation Mediated by Lithium Iodide of Electron-Deficient Alkenes with Activated Dibromomethylene Compounds.
Kawai, Daisuke; Kawasumi, Katsuaki; Miyahara, Tsukasa; Hirashita, Tsunehisa; Araki, Shuki.
Synlett (2008), 2977-2980.

(101) Allylation of methylenecyclopropanes with allylindium reagents.
Hirashita, Tsunehisa; Daikoku, Yusuke; Ogura, Mamiko; Araki, Shuki.
Tetrahedron Letters (2008), 49, 5411-5433.

(100) Radical reactions initiated by the photochemical cleavage of carbon-indium bonds of organoindium compounds.
Hirashita, Tsunehisa; Hayashi, Ayumi; Makoto, Tsuji; Tanaka, Jiro; Araki, Shuki.
Tetrahedron (2008), 64, 2642-2650.

(99) GaCl₃-catalyzed [4+2] annulations of allyltrimethylsilane and trimethyl(propargyl)silane with aldimines.
Hirashita, Tsunehisa; Kawai, Daisuke; Araki, Shuki.
Tetrahedron Letters (2007), 48, 5421-5424.

(98) Cis double allylation of cyclopropenes using cyclopropylindium reagents.
Hirashita, Tsunehisa; Shiraki, Fumio; Onishi, Kenji; Ogura, Mamiko; Araki, Shuki.
Organic & Biomolecular Chemistry (2007), 5, 2154-2158.

(97) Nickel-catalyzed indium(I)-mediated double addition of aldehydes to 1,3-dienes.
Hirashita, Tsunehisa; Kambe, Shinya; Tsuji, Hiromitsu; Araki, Shuki.
Chemical Communications (2006), 2595-2597.

(96) Ni-catalysed bis-allylation of internal alkynes with triallylindium.
Hirashita, Tsunehisa; Akutagawa, Kazuhiko; Kamei,Toshiya; Araki, Shuki.
Chemical Communications (2006), 2598-2600.

(95) Reaction of Hydroxybenzyl Alcohols under Hydrothermal Conditions.
Hirashita, Tsunehisa; Araki, Shuki; Tsuda, Takao; Kitagawa, Shinya; Umeyama, Takayuki; Aoki, Mutsumi; Nakamura, Koichi.
Green Chemistry (2006) 8, 328-329.

(94) Reaction of Allylic-type Diindium Compounds with Electrophiles.
Hirashita, Tsunehisa; Arai, Shun; Mitsui, Kazuma; Makino, Hajime; Araki, Shuki.
Chemistry Letters (2006) 35(3), 314-315.

(93) Stereoselective allylation of azirines with allylindium reagents.
Hirashita, Tsunehisa; Toumatsu, Shinya; Imagawa, Yuri; Araki, Shuki; Setsune, Jun-ichiro.
Tetrahedron Letters (2006), 47(10), 1613-1616.

(92) Photochemical and radical initiator-induced reaction of allylic indium compounds.
Hirashita, Tsunehisa; Tanaka, Jiro; Hayashi, Ayumi; Araki, Shuki.
Tetrahedron Letters (2005), 46(2), 289-292.

(91) Allylation of epoxides with allylic indium reagents.
Hirashita, Tsunehisa; Mitsui, Kazuma; Hayashi, Yousuke; Araki, Shuki.
Tetrahedron Letters (2004), 45(50), 9189-9191.

(90) Direct Preparation of Allylic Indium(III) Reagents from Allylic Alcohols via a Reductive Transmetalation of pai-Allylnickel(II) with Indium(I) Iodide.
Hirashita, Tsunehisa; Kambe, Shinya; Tsuji, Hiromitsu; Omori, Hideki; Araki, Shuki.
Journal of Organic Chemistry (2004), 69(15), 5054-5059.

(89) Reaction of indium ate complexes with allylic compounds. Controlling SN2/SN2' selectivity by solvents.
Hirashita, Tsunehisa; Hayashi, Yousuke; Mitsui, Kazuma; Araki, Shuki.
Tetrahedron Letters (2004), 45(16), 3225-3228.

(88) A new synthesis of pyrroles by the condensation of cyclopropenes and nitriles mediated by gallium(III) and indium(III) salts.
Araki, Shuki; Tanaka, Takashi; Toumatsu, Shinya; Hirashita, Tsunehisa.
Organic & Biomolecular Chemistry (2003), 1(22), 4025-4029.

(87) Control of diastereoselectivity in the crotylation and cinnamylation of aldehydes by the selection of ligands on allylic indium reagents.
Hirashita, Tsunehisa; Kamei, Toshiya; Satake, Makoto; Horie, Tomoaki; Shimizu, Hidetaka; Araki, Shuki.
Organic & Biomolecular Chemistry (2003), 1(21), 3799-3803.

(86) Allylgallation of cyclopropenes. Crystal structure of a novel cyclopropylgallium compound prepared by allylgallation of hydroxy-bearing cyclopropene.
Araki, Shuki; Tanaka, Takashi; Hirashita, Tsunehisa; Setsune, Jun-ichiro.
Tetrahedron Letters (2003), 44(43), 8001-8003.

(85) Reaction cascades initiated by nucleophilic attack of heteropentalene mesomeric betaine and nitrogen-rich mesoionic tetrazolium-5-amides on electron-deficient unsaturated compounds. Synthesis of novel heterocyclic systems.
Araki, Shuki; Kuzuya, Masashi; Hamada, Kenji; Nogura, Masatoshi; Ohata, Nayumi.
Organic & Biomolecular Chemistry (2003), 1(6), 978-983.

(84) A new synthesis of lavandulol via indium/palladium-mediated umpolung of vinyloxirane.
Araki, Shuki; Kambe, Shinya; Kameda, Keiko; Hirashita, Tsunehisa.
Synthesis (2003), (5), 751-754.

(83) Allylic-Type Diindium Reagents. Reactivity toward Electrophiles and Cascade Coupling Reactions with Imines.
Hirashita, Tsunehisa; Hayashi, Yousuke; Mitsui, Kazuma; Araki, Shuki.
Journal of Organic Chemistry (2003), 68(4), 1309-1313.

(82) Stereoselective synthesis of halocyclopropanes via halogenation of cyclopropylindium reagents.
Araki, Shuki; Kenji, Ohnishi; Shiraki, Fumio; Hirashita, Tsunehisa.
Tetrahedron Letters (2002), 43(45), 8033-8035.

(81) The photochemical reactions of nitrogen-rich mesoionic 1,3-diphenyltetrazolium heterocycles and related compounds.
Araki, Shuki; Hattori, Hiromi; Ogawa, Koji; Kuzuya, Masashi; Inoue, Tomoko; Yamamura, Hatsuo; Kawai, Masao.
Journal of the Chemical Society, Perkin Transactions 1 (2001), (19), 2476-2482.

(80) Umpolung of vinyloxiranes: regio- and stereoselectivity of the In/Pd-mediated allylation of carbonyl compounds.
Araki, Shuki; Kameda, Keiko; Tanaka, Jiro; Hirashita, Tsunehisa; Yamamura, Hatsuo; Kawai, Masao.
Journal of Organic Chemistry (2001), 66(23), 7919-7921.

(79) Allylindation of cyclopropenes in organic and aqueous media: switching the regio- and stereoselectivity based on the chelation with a hydroxyl group and the crystal structure of the cyclopropylindium product.
Araki, Shuki; Shiraki, Fumio; Tanaka, Takashi; Nakano, Hiroyuki; Subburaj, Kandasamy; Hirashita, Tsunehisa; Yamamura, Hatsuo; Kawai, Masao.
Chemistry--A European Journal (2001), 7(13), 2784-2790.

(78) A new cascade for the one-pot synthesis of linear homoallylic alcohols with an allylic diindium reagent.
Hirashita, Tsunehisa; Yamamura, Hatsuo; Kawai, Masao; Araki, Shuki.
Chemical Communications (2001), (4), 387-388.

(77) Nitrogen NMR study of some mesoionic oxadiazoles and thiadiazoles.
Jazwinski, Jaroslaw; Staszewska, Olga; Wiench, Jerzy W.; Stefaniak, Lech; Araki, Shuki; Webb, Graham A.
Magnetic Resonance in Chemistry (2000), 38(8), 617-626.

(76) A New Preparative Method for Allylic Indium(III) Reagents by Reductive Transmetalation of p-Allylpalladium(II) with Indium(I) Salts.
Araki, Shuki; Kamei, Toshiya; Hirashita, Tsunehisa; Yamamura, Hatsuo; Kawai, Masao.
Organic Letters (2000), 2(6), 847-849.

(75) A facile preparation of indium enolates and their Reformatskii- and Darzens-type reactions.
Hirashita, Tsunehisa; Kinoshita, Kenji; Yamamura, Hatsuo; Kawai, Masao; Araki, Shuki.
Perkin 1 (2000), (5), 825-828.

(74) Chelation-controlled regio- and stereoselective allylindation of norbornenols.
Araki, Shuki; Kamei, Toshiya; Igarashi, Yukimitsu; Hirashita, Tsunehisa; Yamamura, Hatsuo; Kawai, Masao.
Tetrahedron Letters (1999), 40(45), 7999-8002.

(73) Photochemistry of mesoionic compounds. Photochemical conversion of 5-azido-1,3-diaryltetrazolium salts to novel tricyclic mesoions with a tetrazolo[1,5-a]benzimidazole skeleton.
Araki, Shuki; Hattori, Hiromi; Shimizu, Noriyuki; Ogawa, Koji; Yamamura, Hatsuo; Kawai, Masao.
Journal of Heterocyclic Chemistry (1999), 36(4), 863-867.

(72) Synthesis, electrochemical investigation and EPR spectroscopy of a reversible four-stage redox system based on mesoionic 5,5'-azinobis(1,3-diphenyltetrazole) and related mesoionic compounds.
Araki, Shuki; Yamamoto, Kaori; Inoue, Tomoko; Fujimoto, Koji; Yamamura, Hatsuo; Kawai, Masao; Butsugan, Yasuo; Zhou, Jinkui; Eichhorn, Emerich; Rieker, Anton; Huber, Martina.
Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1999), (5), 985-995.

(71) Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents.
Araki, Shuki; Horie, Tomoaki; Kato, Motoshi; Hirashita, Tsunehisa; Yamamura, Hatsuo; Kawai, Masao.
Tetrahedron Letters (1999), 40(12), 2331-2334.

(70) Preparation of g-Heterosubstituted Allylindium and Diindium Reagents and Their Reactions with Carbonyl Compounds.
Hirashita, Tsunehisa; Kamei, Toshiya; Horie, Tomoaki; Yamamura, Hatsuo; Kawai, Masao; Araki, Shuki.
Journal of Organic Chemistry (1999), 64(1), 172-177.

(69) Stereodivergent allylindation of cyclopropenes. Remarkable stereodirection and acceleration by neighboring carboxyl and hydroxyl groups.
Araki, Shuki; Nakano, Hiroyuki; Subburaj, Kandasamy; Hirashita, Tsunehisa; Shibutani, Kensuke; Yamamura, Hatsuo; Kawai, Masao; Butsugan, Yasuo.
Tetrahedron Letters (1998), 39(35), 6327-6330.

(68) Nitrogen-rich mesoionic compounds from 1,3-diaryl-5-chlorotetrazolium salts and nitrogen nucleophiles. Synthesis and properties of 1,3-diaryl-5-azidotetrazolium salts.
Araki, Shuki; Yamamoto, Kaori; Yagi, Misako; Inoue, Tomoko; Fukagawa, Hiroyo; Hattori, Hiromi; Yamamura, Hatsuo; Kawai, Masao; Butsugan, Yasuo.
European Journal of Organic Chemistry (1998), (1), 121-127.

(67) High g-selectivity in the coupling of penta-2,4-dienyl- and pent-2-en-4-ynylindium reagents with aldehydes.
Hirashita, Tsunehisa; Inoue, Shin'ichirou; Yamamura, Hatsuo; Kawai, Masao; Araki, Shuki.
Journal of Organometallic Chemistry (1997), 549(1-2), 305-309.

(66) Indium-mediated reaction of 1,3-dichloro- and 1,3-dibromopropanes with carbonyl compounds. Generation of novel 3,3-diindiopropene.
Araki, Shuki; Hirashita, Tsunehisa; Shimizu, Hidetaka; Yamamura, Hatsuo; Kawai, Masao; Butsugan, Yasuo.
Tetrahedron Letters (1996), 37(46), 8417-8420.

(65) Regio- and Stereoselective Allylindation of Allenols Regulated by a Hydroxyl-Chelated Bicyclic Transition State.
Araki, Shuki; Usui, Hidenao; Kato, Motoshi; Butsugan, Yasuo.
Journal of the American Chemical Society (1996), 118(19), 4699-4700.

(64) Reaction of a-halo organoindium reagents with carbonyl compounds and electron-deficient alkenes.
Araki, Shuki; Hirashita, Tsunehisa; Shimizu, Ken; Ikeda, Takahiro; Butsugan, Yasuo.
Tetrahedron (1996), 52(8), 2803-2816.

Book

(8) "Indium Compounds"
Araki, Shuki and Hirashita, Tsunehisa.
in "Science of Synthesis" ed By E. M. Carreira et al.,
Thieme Chemistry, Stuttgart, in press.

(7) "Indium(III) Iodide"
Hirashita, Tsunehisa. and Araki, Shuki.
in "Electronic Encyclopedia of Reagents for Organic Synthesis" ed. By A. Charette,
John Wiley & Sons, London, in press.

(6) "Indium and Gallium"
Araki, Shuki and Hirashita, Tsunehisa.
in "Comprehensive Organometallic Chemistry III" ed by R. Crabtree and M. Mingos,
Elsevier, Oxford, 649-751, 2007.

(5) "Methyl lithium"
Araki, Shuki and Hirashita, Tsunehisa.
in "Electronic Encyclopedia of Reagents for Organic Synthesis" ed. By L. A. Paquette,
John Wiley & Sons, London, 2006.

(4) "In in Organic Synthesis"
Araki, Shuki and Hirashita, Tsunehisa.
in "Main Group Metals in Organic Synthesis" ed. By H. Yamamoto and K. Oshima,
Wiley-VCH, Weinheim, 2004; Vol 1, pp 323-386.

(3) "Indium(I) Iodide"
Araki, Shuki and Hirashita, Tsunehisa.
in "Electronic Encyclopedia of Reagents for Organic Synthesis" ed. By L. A. Paquette,
John Wiley & Sons, London, 2002.

(2) "Indium Trichloride"
Araki, Shuki and Hirashita, Tsunehisa.
in "Electronic Encyclopedia of Reagents for Organic Synthesis" ed. By L. A. Paquette,
John Wiley & Sons, London, 2002.