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Development of new reactions using iron phthalocyanineand molecularoxygen

Research Project

Project/Area Number 23790008
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKanazawa University

Principal Investigator

TANIGUCHI Tsuyoshi  金沢大学, 薬学系, 薬学系 (60444204)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2012: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords鉄触媒 / ラジカル反応 / 分子状酸素 / C-H 酸化 / 縮合反応 / 触媒反応 / C-H酸化
Research Abstract

Three novel reactions using iron phthalocyanine and molecular oxygen have been developed:
(1) a new method for generation of radicals from hydrazine compounds and addition reactions of resultant radicals to alkenes
(2) synthesis of 1,4-diols from simple alkenes by redox hydration using sodium borohydride
(3) oxidation-reduction esterification using oxygen as an oxidant. In addition, mild oxynitration reactions of alkenes have been found in the courseof these studies.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (33 results)

All 2013 2012 2011 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (21 results) Remarks (2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Multifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation2013

    • Author(s)
      Tsuyoshi Taniguchi, Yuki sugiura, Takashi Hatta, Atsushi Yajima, Hiroyuki Ishibashi
    • Journal Title

      Chemical Communications

      Volume: 49 Issue: 22 Pages: 2198-2200

    • DOI

      10.1039/c3cc00130j

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Recyclable Mitsunobu Reagents: Catalytic Mitsunobu Reactions with an Iron Catalyst and Atomospheric Oxygen2013

    • Author(s)
      Daisuke Hirose, Tsuyoshi Taniguchi, Hiroyuki Ishibashi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 17 Pages: 4613-4617

    • DOI

      10.1002/anie.201300153

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Zaimoku, Hisaaki; Nishide, Hiroshi; Nishibata, Asami; Goto, Naoya; Taniguchi, Tsuyoshi; Ishibashi, Hiroyuki2013

    • Author(s)
      Syntheses of (±)-Serratine, (±)-Lycoposerramine T, and (±)-Lycopoclavamine B
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 9 Pages: 2140-2143

    • DOI

      10.1021/ol400628h

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iodine-Mediated α-Acetoxylation of 2,3-Disubstituted Indoles2012

    • Author(s)
      Hisaaki Zaimoku, Takashi Hatta, Tsuyoshi Taniguchi, Hiroyuki Ishibashi
    • Journal Title

      Org. Lett

      Volume: 14 Issue: 23 Pages: 6088-6091

    • DOI

      10.1021/ol302983t

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the Core of Actinophyllic Acid Using a Transannular Acyl Radical Cyclization2012

    • Author(s)
      Hisaaki Zaimoku, Tsuyoshi Taniguchi, Hiroyuki Ishibashi
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 6 Pages: 1656-1658

    • DOI

      10.1021/ol300280s

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Esterification via Iron-Catalyzed Activation of Triphenylphosphine with Air2011

    • Author(s)
      Tsuyoshi Taniguchi, Daisuke Hirose, Hiroyuki Ishibashi
    • Journal Title

      ACS Catal

      Volume: 1 Issue: 11 Pages: 1469-1474

    • DOI

      10.1021/cs2003824

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Oxidative NItration of Alkenes with tert-Butyl Nitrite and Oxygen2011

    • Author(s)
      Tsuyoshi Taniguchi, Atsushi Yajima, Hiroyuki Ishibashi
    • Journal Title

      Adv. Synth. Catal

      Volume: 353 Pages: 2643-2647

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Iron-catalyzed sulfonyl radical formations from sulfonylhydrazides and oxidative addition to alkenes2011

    • Author(s)
      Tsuyoshi Taniguchi, Atsushi Idota, Hiroyuki Ishibashi
    • Journal Title

      Org. Biomol. Chem

      Volume: 9 Issue: 9 Pages: 3151-3153

    • DOI

      10.1039/c0ob01119c

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of -hydroxyphosphonates by iron-catalyzed oxidative addition of phosphonyl radicals to alkenes2011

    • Author(s)
      Tsuyoshi Taniguchi, Atsushi Idota, Shin'ichi Yokoyama, Hiroyuki Ishibashi
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Issue: 37 Pages: 4768-4770

    • DOI

      10.1016/j.tetlet.2011.07.026

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 鉄触媒と空気を用いる光延試薬の触媒化2013

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Related Report
      2012 Annual Research Report
  • [Presentation] (-)-Serratineおよびその誘導体の不斉合成研究 Synthetic Studies of (-)-Serratine and Related Compounds2013

    • Author(s)
      材木久晃、西出洋志、後藤直也、西端亜紗美、谷口剛史、石橋弘行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒による空気酸化を利用するエステル化反応の反応機構解析2012

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      日本薬学会第132 年会
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Related Report
      2012 Final Research Report
  • [Presentation] 鉄触媒を用いたラジカル的 C-H 酸素酸化を経由するアルケンからの1,4-ジオール合成2012

    • Author(s)
      橋本卓磨、谷口剛史、石橋弘行
    • Organizer
      日本薬学会第132 年会
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Related Report
      2012 Final Research Report
  • [Presentation] 鉄触媒と酸素を用いる触媒的光延反応の開発2012

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Lycopodium アルカロイド serratine および lycoposerramine T の全合成2012

    • Author(s)
      材木久晃、西出洋志、後藤直也、西端亜紗美、谷口剛史、石橋弘行
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都テルサ(京都府京都市)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒と空気を再酸化剤とする触媒的光延反応の開発2012

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      平成24年度有機合成化学北陸セミナー
    • Place of Presentation
      富山観光ホテル(富山県富山市)
    • Related Report
      2012 Annual Research Report
  • [Presentation] ヨウ素試薬を活用するインドール化合物の緩和なα-アセトキシ化反応の開発2012

    • Author(s)
      材木久晃、八田喬史、谷口剛史、石橋弘行
    • Organizer
      平成24年度有機合成化学北陸セミナー
    • Place of Presentation
      富山観光ホテル(富山県富山市)
    • Related Report
      2012 Annual Research Report
  • [Presentation] (±)-Serratine および(±)-Lycoposerramine T の全合成2012

    • Author(s)
      材木久晃、西出洋志、後藤直也、西端亜紗美、谷口剛史、石橋弘行
    • Organizer
      平成24年度有機合成化学北陸セミナー
    • Place of Presentation
      富山観光ホテル(富山県富山市)
    • Related Report
      2012 Annual Research Report
  • [Presentation] αーフルオロヒドラゾン誘導体のC-F 結合切断を伴う置換反応2012

    • Author(s)
      柚木良太、八島 淳、谷口剛史、石橋弘行
    • Organizer
      平成24年度有機合成化学北陸セミナー
    • Place of Presentation
      富山観光ホテル(富山県富山市
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒による空気酸化を利用するエステル化反応の反応機構解析2012

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒を用いたラジカル的C-H酸素酸化を経由するアルケンからの1,4-ジオー2012

    • Author(s)
      橋本卓磨、谷口剛史、石橋弘行
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒によるトリフェニルホスフィンの空気酸化を利用したエステル化反応の速度論解析2011

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      有機合成化学北陸セミナー
    • Place of Presentation
      港のホテル(福井県福井市)
    • Related Report
      2012 Final Research Report
  • [Presentation] 鉄触媒を用いる単純アルケンの水和反応と直截的 C-H 酸素酸化を経る 1,4-ジオールの合成2011

    • Author(s)
      橋本卓磨、谷口剛史、石橋弘行
    • Organizer
      有機合成化学北陸セミナー
    • Place of Presentation
      港のホテル(福井県福井市)
    • Related Report
      2012 Final Research Report
  • [Presentation] フタロシアニン鉄(II)と酸素を用いるトリフェニルホスフィンの酸化的活性化を経るエステル化反応2011

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      熊本市民会館(熊本県熊本市)
    • Related Report
      2012 Final Research Report
  • [Presentation] 亜硝酸エステルと酸素を用いた不活性メチル基のC-H 酸化を経るアルケンの多官能基化反応2011

    • Author(s)
      杉浦祐基、八島淳、谷口剛史、石橋弘行
    • Place of Presentation
      熊本市民会館(熊本県熊本市)
    • Related Report
      2012 Final Research Report
  • [Presentation] Iron-catalyzed Redox Esterification Using Air as an Oxidant2011

    • Author(s)
      Tsuyoshi Taniguchi, Daisuke Hirose, Hiroyuki Ishibashi
    • Organizer
      The 2nd International Symposium on Process Chemistry
    • Place of Presentation
      Kyoto International
    • Related Report
      2012 Final Research Report
  • [Presentation] Iron- or Oxygen-Mediated Radical Nitration of Alkenes2011

    • Author(s)
      Tsuyoshi Taniguchi
    • Organizer
      5th Pacific Symposium on Radical Chemistry
    • Place of Presentation
      Hotel Seamore (Shirahama, Japan)
    • Related Report
      2012 Final Research Report
  • [Presentation] 鉄触媒によるトリフェニルホスフィンの空気酸化を利用したエステル化反応の速度論的解析2011

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      有機合成化学北陸セミナー
    • Place of Presentation
      港のホテル(福井県坂井市)
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒を用いる単純アルケンの水和反応と直接的C-H酸素酸化を経る1,4-ジオールの合成2011

    • Author(s)
      橋本卓磨、谷口剛史、石橋弘行
    • Organizer
      有機合成化学北陸セミナー
    • Place of Presentation
      港のホテル(福井県坂井市)
    • Related Report
      2011 Research-status Report
  • [Presentation] フタロシアニン鉄(II)と酸素を用いるトリフェニルホスフィンの酸化的活性化を経るエステル化反応2011

    • Author(s)
      廣瀬大祐、谷口剛史、石橋弘行
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      熊本市民会館(熊本県熊本市)
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://www.p.kanazawa-u.ac.jp/~gousei/

    • Related Report
      2012 Final Research Report
  • [Remarks]

    • URL

      http://www.p.kanazawa-u.ac.jp/~gousei/

    • Related Report
      2011 Research-status Report
  • [Patent(Industrial Property Rights)] 反応方法及びそれに用いる新規アゾ化合物2013

    • Inventor(s)
      谷口剛史、石橋弘行、廣瀬大祐
    • Industrial Property Rights Holder
      国立大学法人金沢大学
    • Industrial Property Number
      2013-017504
    • Filing Date
      2013-01-31
    • Related Report
      2012 Annual Research Report 2012 Final Research Report

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Published: 2011-08-05   Modified: 2019-07-29  

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