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Selective functionalization of aromatic ring through C-C bond formation by photocatalysis

Research Project

Project/Area Number 24656490
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Catalyst/Resource chemical process
Research InstitutionKyoto University (2013)
Nagoya University (2012)

Principal Investigator

YOSHIDA Hisao  京都大学, 人間・環境学研究科(研究院), 教授 (80273267)

Co-Investigator(Renkei-kenkyūsha) KUMAGAI Jun  名古屋大学, エコトピア科学研究所, 准教授 (20303662)
YOSHIDA Tomoko  名古屋大学, エコトピア科学研究所, 准教授 (90283415)
Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords化学合成 / 光触媒 / パラジウム触媒 / 芳香族官能基化 / シアノメチル化 / 芳香環官能基化 / 水素 / 炭素-炭素結合形成 / 芳香族
Research Abstract

Functionalization of aromatic ring are usually carried out under sever condition via multistep with large consumption and emission of chemicals. This motivates us to develop novel and environmentally-begin simple chemical processes that can be operated under mild condition. In this study, we successfully found that a palladium loaded titanium oxide photocatalyst could promote a simple reaction from benzene and acetonitrile to produce benzyl cyanide and hydrogen through a unique carbon-carbon bond formation. We also found that the photocatalyst functioned as a hybridized catalyst where the loaded palladium nano-particle acted as not only a reduction sites for hydrogen formation (cocatalyst of photocatalyst) but also a catalyst to directly activate benzene molecule.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (31 results)

All 2014 2013 2012 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (22 results) (of which Invited: 3 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Direct introduction of OH group to sp^2-carbon on platinum-loaded titanium oxide photocatalyst2014

    • Author(s)
      H. Yuzawa, H. Yoshida
    • Journal Title

      Topics in Catal.

      Volume: 57 Issue: 10-13 Pages: 984-994

    • DOI

      10.1007/s11244-014-0261-0

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Direct functionalization of aromatic rings on platinum -loaded titanium oxide photocatalyst2013

    • Author(s)
      H. Yuzawa, H. Yoshida
    • Journal Title

      Chem. Lett.

      Volume: 42 Issue: 11 Pages: 1336-1343

    • DOI

      10.1246/cl.130757

    • NAID

      130004426809

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Reaction mechanism of aromatic ring amination of benzene and substituted benzenes by aqueous ammonia over platinum-loaded titanium oxide photocatalyst2013

    • Author(s)
      H. Yuzawa, J. Kumagai, H. Yoshida
    • Journal Title

      J. Phys. Chem. C

      Volume: 117 Pages: 11047-11058

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] A heterogeneous palladium catalyst hybridised with a titanium dioxide photocatalyst for direct C−C bond formation between an aromatic ring and acetonitrile2013

    • Author(s)
      H. Yoshida, Y. Fujimura, H. Yuzawa, J. Kumagai, T. Yoshida
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 36 Pages: 3793-3795

    • DOI

      10.1039/c3cc41068d

    • Related Report
      2013 Annual Research Report 2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Anti-Markovnikov hydration of alkenes over platinum-loaded titanium oxide photocatalyst2013

    • Author(s)
      H. Yuzawa, S. Yoneyama, A. Yamamoto, M. Aoki, K. Otake, H. Itoh, H. Yoshida
    • Journal Title

      Catal. Sci. Technol.

      Volume: 3 Issue: 7 Pages: 1739-1749

    • DOI

      10.1039/c3cy00019b

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Reaction mechanism of aromatic ring hydroxylation by water over platinum-loaded titanium oxide photocatalyst2012

    • Author(s)
      H. Yuzawa, M. Aoki, K. Otake, T. Hattori, H. Itoh, H. Yoshida
    • Journal Title

      J. Phys. Chem. C

      Volume: 116 Issue: 48 Pages: 25376-25387

    • DOI

      10.1021/jp308453d

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Reaction Mechanism of Ammonia Decomposition to Nitrogen and Hydrogen over Metal Loaded Titanium Oxide Photocatalyst2012

    • Author(s)
      湯沢勇人
    • Journal Title

      Journal of Physical Chemistry C

      Volume: 116 Issue: 6 Pages: 4126-4136

    • DOI

      10.1021/jp209795t

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Presentation] パラジウム添加酸化チタン光触媒を用いたピリジンのシアノメチル化反応2014

    • Author(s)
      竹内智亮,藤村祐樹,吉田寿雄
    • Organizer
      第113回触媒討論会
    • Place of Presentation
      ロワジールホテル豊橋
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] 光触媒ハイブリッドパラジウム触媒によるベンゼンの直接シアノメチル化2014

    • Author(s)
      吉田寿雄
    • Organizer
      新学術領域研究「分子活性化」 第6回公開シンポジウム
    • Place of Presentation
      東京工業大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] いくつかの光触媒反応とそのメカニズム2013

    • Author(s)
      吉田寿雄
    • Organizer
      平成25年度第2回キャタリストクラブ例会
    • Place of Presentation
      関西大学
    • Year and Date
      2013-11-01
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] Reaction mechanism of photocatalytic ammonia decomposition over metal loaded titanium oxide2013

    • Author(s)
      H. Yoshida
    • Organizer
      11th Symposium of Research Center for Solar Energy Chemistry
    • Place of Presentation
      Graduate School of Engineering Science, Osaka University
    • Year and Date
      2013-02-20
    • Related Report
      2013 Final Research Report
  • [Presentation] 貴金属添加酸化チタン光触媒を用いた水素生成を伴う芳香環直接官能基化反応2013

    • Author(s)
      吉田寿雄
    • Organizer
      次世代ESICBセミナー2013
    • Place of Presentation
      京都大学桂キャンパス
    • Year and Date
      2013-02-08
    • Related Report
      2013 Final Research Report
  • [Presentation] Anti-Markovnikov hydration of alkenes over platinum-loaded titanium oxide photocatalyst2013

    • Author(s)
      Hisao Yoshida, Hayato Yuzawa, Shoko Yoneyama, Akihito Yamamoto, Hideaki Itoh
    • Organizer
      Pre-Symposium of C&FC 2013 + Cat-on-Cat
    • Place of Presentation
      Himeji Egret
    • Related Report
      2013 Final Research Report
  • [Presentation] Addition of alcohol to benzene with C-C bond formation on Pt loaded titanium oxide photocatalyst2013

    • Author(s)
      Tomoaki Takeuchi, Yuki Fujimura, Hisao Yoshida
    • Organizer
      Pre-Symposium of C&FC 2013 + Cat-on-Cat
    • Place of Presentation
      Himeji Egret
    • Related Report
      2013 Final Research Report
  • [Presentation] 白金添加酸化チタンを用いたベンゼンへの光触媒的アルコール付加反応2013

    • Author(s)
      竹内智亮,藤村祐樹,吉田寿雄
    • Organizer
      第112回触媒討論会
    • Place of Presentation
      秋田大学手形キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] Anti-Markovnikov hydration of alkenes over platinum-loaded titanium oxide photocatalyst2013

    • Author(s)
      H. Yuzawa, S. Yoneyama, A. Yamamoto, M. Aoki, K. Otake, H. Itoh, H. Yoshida
    • Organizer
      第11回触媒化学ワークショップ
    • Place of Presentation
      松本市駅前会館
    • Related Report
      2013 Final Research Report
  • [Presentation] 白金添加酸化チタン光触媒によるベンゼンへのアルコール付加反応2013

    • Author(s)
      竹内智亮,吉田寿雄
    • Organizer
      第11回触媒化学ワークショップ
    • Place of Presentation
      松本市駅前会館
    • Related Report
      2013 Final Research Report
  • [Presentation] Direct functionalization of aromatic ring with hydrogen formation by metal-loaded titanium oxide photocatalysts2012

    • Author(s)
      Hisao Yoshida
    • Organizer
      Seminar at Ibnu Sina Institute for Fundamental Science Studies, Universiti Teknologi Malasia (UTM)
    • Place of Presentation
      Johor Bahru, Malaysia
    • Year and Date
      2012-12-14
    • Related Report
      2013 Final Research Report
  • [Presentation] 貴金属添加酸化チタン光触媒を用いた水素生成を伴う芳香環直接官能基化反応2012

    • Author(s)
      吉田寿雄
    • Organizer
      触媒学会北海道支部札幌講演会
    • Place of Presentation
      北海道大学工学部
    • Year and Date
      2012-12-07
    • Related Report
      2013 Final Research Report
  • [Presentation] 光触媒を用いた水素生成を伴う芳香族直接官能基化反応2012

    • Author(s)
      吉田寿雄
    • Organizer
      愛媛大学工学部応用化学科,平成24年度応用化学科セミナー,第182回ミニシンポジウム
    • Place of Presentation
      愛媛大学工学部南加記念ホール
    • Year and Date
      2012-07-27
    • Related Report
      2013 Final Research Report
  • [Presentation] Direct functionalization of benzene by acetonitrile with palladium-loaded titanium oxide photocatalyst2012

    • Author(s)
      H. Yoshida, Y. H. Yoshida, Y. Fujimura
    • Organizer
      ICC 2012 Poster Symposia, PS.11"Versatile TiO2-based photocatalysts"
    • Place of Presentation
      Munich, Germany
    • Year and Date
      2012-07-02
    • Related Report
      2013 Final Research Report
  • [Presentation] Photocatalytic C-C bond formation between aromatic ring and acetonitrile2012

    • Author(s)
      Hisao Yoshida, Yuki Fujimura, and Hayato Yuzawa
    • Organizer
      12th Tateshina Conference on Organic Chemistry
    • Place of Presentation
      Tateshina Forum, Tateshina, Japan
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Presentation] 酸化チタン光触媒を用いたベンゼンシアノメチル化反応における水の共存効果2012

    • Author(s)
      藤村祐樹,吉田寿雄
    • Organizer
      第110回触媒討論会
    • Place of Presentation
      九州大学伊都キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] Direct functionalization of aromatic ring with hydrogen formation by metal-loaded titanium oxide photocatalysts2012

    • Author(s)
      H. Yoshida
    • Organizer
      The International Symposium on Photocatalysis
    • Place of Presentation
      Kyoto, Japan
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Presentation] Direct functionalization of benzene by acetonitrile with palladium-loaded titanium oxide photocatalyst2012

    • Author(s)
      H. Yoshida, Y. Fujimura
    • Organizer
      15th International Congress on Catalysis 2012 (15th ICC 2012)
    • Place of Presentation
      Munich, Germany
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Presentation] 酸化チタン光触媒を用いたベンゼンシアノメチル化反応における水の共存効果2012

    • Author(s)
      藤村祐樹・吉田寿雄
    • Organizer
      第110回触媒討論会
    • Place of Presentation
      九州大学,伊都キャンパス(福岡県)
    • Related Report
      2012 Research-status Report
  • [Presentation] 光触媒を用いた水素生成を伴う芳香族直接官能基化反応

    • Author(s)
      吉田寿雄
    • Organizer
      平成24年度 応用化学科セミナー,第182回 ミニシンポジウム
    • Place of Presentation
      愛媛大学,工学部南加記念ホール(愛媛県)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 貴金属添加酸化チタン光触媒を用いた水素生成を伴う芳香環直接官能基化反応

    • Author(s)
      吉田寿雄
    • Organizer
      触媒学会 北海道支部 札幌講演会
    • Place of Presentation
      北海道大学工学部B32講義室(北海道)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 貴金属添加酸化チタン光触媒を用いた水素生成を伴う芳香環直接官能基化反応

    • Author(s)
      吉田寿雄
    • Organizer
      次世代ESICBセミナー2013
    • Place of Presentation
      京都大学桂キャンパスAクラスター(京都府)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Book] 太陽エネルギー社会を築く材料テクノロジー(II)材料プロセス編,6章光を利用した物質変換2013

    • Author(s)
      吉田寿雄
    • Publisher
      コロナ社(ISBN978-4-339-06628-9)
    • Related Report
      2013 Final Research Report
  • [Remarks]

    • URL

      http://yoshida.jinkan.kyoto-u.ac.jp/

    • Related Report
      2013 Final Research Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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