Development of novel C-C bond formation based on activation of multiple bonds using cationic species

• Project/Area Number: 20750026
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Chiba University
• Principal Investigator: MATSUMOTO Shoji Chiba University, 大学院・工学研究科, 准教授 (50302534)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2009: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 合成化学 / カチオン / 多重結合 / 環化反応 / 光反応 / ヨウ素 / 環境調和 / 付加反応 / 置換反応 / ヨウ化水素 / 二面角 / チオピラン / ジヒドロキノリン / 蛍光 / ベンゼン誘導体

Research Abstract

I achieved the development of new types of reaction including carbon-carbon bond and carbon-sulfur bond formations based on the activation of multiple bonds using cationic species derived from molecular iodine or hydrogen iodide. The intra- and intermolecular reactions gave the corresponding cyclic compounds. In the case of the intramolecular reactions, I found that a structure as well as a substituent of the reactant are important to make the cyclization reaction. I also obtained the luminescent materials when the reaction of intermolecular carbon-carbon bond formation proceeded. It is suggested that these reactions can be applied to the formation of useful functional materials.

Research Products

• [Journal Article] ヨウ素および(ポリ)ヨウ化水素を用いた多重結合活性化による環構造構築反応 (2011)
  • Author(s): 松本祥治, 小倉克之
  • Journal Title: 有機合成化学協会誌 Vol.69, No.2 Pages: 147-158
  • NAID: 10027916484
  • Peer Reviewed
• [Journal Article] ヨウ素および(ポリ)ヨウ化水素を用いた多重結合活性化による環構造構築反応 (2011)
  • Author(s): 松本祥治・小倉克之
  • Journal Title: 有機合成化学協会誌 Volume: 69巻 Pages: 147-158
  • NAID: 10027916484
  • Peer Reviewed
• [Journal Article] Novel Formation of Dipyrrolo- and Diindolo[1,2-a:2',1'-c]quinoxaline Derivatives and Their Optical Properties (2010)
  • Author(s): Shoji Matsumoto, Sheng Qu, Takamitsu Kobayashi, Masahiro Kanehiro, Motohiro Akazome, Katsuyuki Ogura
  • Journal Title: Heterocycles Vol.80, No.1 Pages: 645-656
  • NAID: 40016900136
  • Peer Reviewed
• [Journal Article] Formation of 1,2-Dihydro-quinoline-3-carboxylic Acid Derivatives from Methyl 3-(Arylamino)acrylates with Hydrogen Iodide (2010)
  • Author(s): Shoji Matsumoto, Takahiro Mori, Motohiro Akazome
  • Journal Title: Synthesis No.21 Pages: 3615-3622
  • Peer Reviewed
• [Journal Article] Formation of 1,2-Dihydroquinoline-3-carboxylic Acid Derivatives from Methyl 2-(Arylamino)acrylates with Hydrogen Iodide (2010)
  • Author(s): S.Matsumoto, T.Mori, M.Akazome
  • Journal Title: Synthesis Volume: No.21 Pages: 3615-3622
  • Peer Reviewed
• [Journal Article] Novel Formation of Dipyrrolo- and Diindolo[1,2-a:2',1'-c]quinoxaline Derivatives and Their Optical Properties (2010)
  • Author(s): S.Matsumoto, S.Qu, T.Kobayashi, M.Kanehiro, M.Akazome, K.Ogura
  • Journal Title: Heterocycles 80 Pages: 645-656
  • NAID: 40016900136
  • Peer Reviewed
• [Journal Article] Synthesis and Physical Properties of Various Organic Dyes Derived from a Single Core Skeleton, 1,2-Dihydroindol-3-one (2009)
  • Author(s): Shoji Matsumoto, Daisuke Samata, Motohiro Akazome, Katsuyuki Ogura
  • Journal Title: Tetrahedron Lett. Vol.50, No.1 Pages: 111-114
  • Peer Reviewed
• [Journal Article] Electric Conductivity in the Complex of Mesoionic anhydro-3-Hydroxythiazolo[3,2-a]pyridinium Hydroxide with Iodine (2009)
  • Author(s): Shoji Matsumoto, Kazuto Kimura, Takeru Sano, Motohiro Akazome, Katsuyuki Ogura
  • Journal Title: J.Photopoly.Sci.Tech. Vol.22, No.5 Pages: 677-678
  • NAID: 130004464779
• [Journal Article] Electric Conductivity in the Complex of Mesoionic anhydro-3-Hydroxy-thiazolo[3,2-a]pyridinium Hydroxide with Iodine (2009)
  • Author(s): S.Matsumoto, K.Kimura, T.Sano, M.Akazome, K.Ogura
  • Journal Title: J.Photopoly.Sci.Tech. 22 Pages: 677-678
• [Journal Article] Synthesis and physical properties of various organic dyes derived from a single core skeleton, 1, 2-dihydroindol-3-one (2009)
  • Author(s): S. Matsumoto, D. Samata, M. Akazome, K. Ogura
  • Journal Title: Tetrahedron Lett 50 Pages: 111-114
  • Peer Reviewed
• [Presentation] Novel Formation of Iodobenzne Derivatives from 1-(Methylthio)-1,3-alkadien-5-ynes via Iodine-induced C-C Bond Formation (2010)
  • Author(s): Shoji Matsumoto, Kenji Takase, Masato Kimura, Hitohiro Nishimura, Keisuke Sakamoto, Motohiro Akazome
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu (U.S.A.)
  • Year and Date: 2010-12-17
• [Presentation] Novel formation of iodobenzne derivatives from 1-(methylthio)-1,3-alkadien-5-ynes via iodine-induced C-C bond formation (2010)
  • Author(s): S.Matsumoto, K.Takase, M.Kimura, H.Nishimura, K.Sakamoto, M.Akazome
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu (U.S.A.)
  • Year and Date: 2010-12-17
• [Presentation] ジヒドロキノリン誘導体合成におけるヨウ化水素生成法の影響 (2010)
  • Author(s): 松本祥治, 森隆浩, 赤染元浩
  • Organizer: 第13回ヨウ学会シンポジウム
  • Place of Presentation: 千葉大学(千葉)
  • Year and Date: 2010-11-09
• [Presentation] (2010)
  • Author(s): 松本祥治, 森隆浩, 赤染元浩
  • Organizer: 1,2-ジヒドロ-3-カルボキシキノリン誘導体の蛍光特性
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-29
• [Presentation] 1,2-ジヒドロ-3-カルボキシキノリン誘導体の蛍光特性 (2010)
  • Author(s): 松本祥治, 森隆浩, 赤染元浩
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-29
• [Presentation] (2010)
  • Author(s): 松本祥治, 影山裕一, 西村仁宏, 赤染元浩
  • Organizer: 1-メチルチオ-3-トシル-1-ヘキセン-5-イン誘導体とヨウ素の反応
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-27
• [Presentation] 1-メチルチオ-3-トシル-1-ヘキセン-5-イン誘導体とヨウ素の反応 (2010)
  • Author(s): 松本祥治, 影山裕一, 西村仁宏, 赤染元浩
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-27
• [Presentation] ヨウ化水素と3-(アリールアミノ)アクリル酸エステルによる新規ジヒドロキノリン誘導体生成反応 (2009)
  • Author(s): 松本祥治, 森隆浩, 赤染元浩
  • Organizer: 第12回ヨウ素学会シンポジウム
  • Place of Presentation: 千葉大学(千葉)
  • Year and Date: 2009-10-29
• [Presentation] ヨウ化水素と3-(アリールアミノ)アクリル酸エステルによる新規ジヒドロキノリン誘導体生成反応 (2009)
  • Author(s): 松本祥治, 森隆浩, 赤染元浩
  • Organizer: 第12回ヨウ学会シンポジウム
  • Place of Presentation: 千葉大学(千葉)
  • Year and Date: 2009-10-29
• [Presentation] Electric Conductivity in the Complex of Mesoionic anhydro-3-Hydroxythiazolo[3,2-a]pyridinium Hydroxide with Iodine (2009)
  • Author(s): Shoji Matsumoto, Kazuto Kimura, Takeru Sano, Motohiro Akazome, Katsuyuki Ogura
  • Organizer: The 26th International Conference of Photopolymer Science and Technology : Materials & Processes for Advanced Microlithography and Nanotechnology
  • Place of Presentation: 千葉大学(千葉)
  • Year and Date: 2009-07-03
• [Presentation] Electric Conductivity in the Complex of Mesoionic anhydro-3-Hydroxy-thiazolo[3,2-a]pyridinium Hydroxide with Iodine (2009)
  • Author(s): S.Matsumoto, K.Kimura, T.Sano, M.Akazome, K.Ogura
  • Organizer: The 26^<th> International Conference of Photopolymer Science and Technology : Materials & Processes for Advanced Microlithography and Nanotechnology
  • Place of Presentation: 千葉大学(千葉)
  • Year and Date: 2009-07-03
• [Presentation] 3-(アリールアミノ)アクリル酸エステルと酸による新規ジヒドロキノリン誘導体生成反応 (2009)
  • Author(s): 松本祥治, 森隆浩, 木村真人, 赤染元浩
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学(千葉)
  • Year and Date: 2009-03-27
• [Presentation] アルキン部位とチオビニル部位間での炭素-炭素結合形成によるヨウ素置換芳香族化合物の生成反応 (2008)
  • Author(s): 松本祥治, 木村真人, 西村仁宏, 小倉克之
  • Organizer: 第35回有機典型元素化学討論会
  • Place of Presentation: 首都大学東京(東京)
  • Year and Date: 2008-12-11
• [Presentation] 3-アリール-1-メチルチオ-1,3-ヘキサジエン-5-インのヨウ素分子によるヨードベンゼン誘導体生成反応 (2008)
  • Author(s): 松本祥治, 西村仁宏, 小倉克之
  • Organizer: 第11回ヨウ素学会シンポジウム
  • Place of Presentation: 千葉大学(千葉)
  • Year and Date: 2008-11-07
• [Presentation] 3-アリール-1-メチルチオ-1, 3-ヘキサジエン-5-インのヨウ素分子によるヨードベンゼン誘導体生成反応 (2008)
  • Author(s): 松本祥治, 西村仁宏, 小倉克之
  • Organizer: 第11回ヨウ学会シンポジウム
  • Place of Presentation: 千葉大学(千葉)
  • Year and Date: 2008-11-07
• [Presentation] Formation of Iodobenzene Derivatives from 1-(Methylthio)-1,3-hexadien-5-ynes : The Effect of Aryl Group at the 3 Position (2008)
  • Author(s): Shoji Matsumoto, Hitohiro Nishimura, Katsuyuki Ogura
  • Organizer: International Meeting on Fluorinated-Peptide Chemistry
  • Place of Presentation: お茶の水女子大学(東京)
  • Year and Date: 2008-11-04
• [Presentation] Formation of Iodobenzene Derivatives from 1-(Methylthio)-1, 3-hexadi-en-5-ynes : The effect of Aryl Group at the 3 Position (2008)
  • Author(s): S. Matsumoto, H. Nishimura, K. Ogura
  • Organizer: International Meeting on Fluorinated-Peptide Chemistry
  • Place of Presentation: お茶の水女子大学(東京)
  • Year and Date: 2008-11-04