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Development of Novel Aerobic Oxidative Dehydrogenation Reactions by Supported Metal Catalysts

Research Project

Project/Area Number 15H06143
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Catalyst/Resource chemical process
Research InstitutionThe University of Tokyo

Principal Investigator

JIN XIONGJIE  東京大学, 大学院工学系研究科(工学部), 特任研究員 (00761412)

Project Period (FY) 2015-08-28 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords担持金属ナノ粒子触媒 / 分子状酸素 / 脱水素 / 酸素化 / 芳香環形成反応 / 脱水素型クロスカップリング反応 / 担持金属触媒 / 脱水素反応 / 酸素化反応 / 脱水素型クロスカップリング
Outline of Final Research Achievements

In this study, several aerobic oxidative dehydrogenation reactions have successfully been developed using supported metal catalysts. For example, (1) Au/OMS-2-catalyzed dehydrogenation of β-heteroatom substituted ketones to the corresponding α,β-unsaturated ketones, (2) Au-Pd/LDH-catalyzed dehydrogenation of cyclohexanols and cyclohexanones to phenols, and (c) Au/Al2O3-catalyzed α-oxygenation of secondary and tertiary amines to the corresponding amides, have been successfully developed. These reactions utilize molecular oxygen as the terminal oxidant and produce water as the sole by-product, which demonstrates the environmentally benign nature of these reactions. A Pd/NiMgAl_LTH-catalyzed acceptorless dehydrogenative aromatization of cyclohexanols, cyclohexanones and cyclohexylamines has also been developed.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • Research Products

    (28 results)

All 2017 2016 2015 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Acknowledgement Compliant: 9 results,  Open Access: 2 results) Presentation (18 results) (of which Int'l Joint Research: 3 results) Remarks (1 results)

  • [Journal Article] A Ni-Mg-Al layered triple hydroxide-supported Pd catalyst for heterogeneous acceptorless dehydrogenative aromatization2017

    • Author(s)
      Jin, X.; Taniguchi, K.; Yamaguchi, K.; Nozaki, K.; Mizuno, N.
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 38 Pages: 5267-5270

    • DOI

      10.1039/c7cc01182b

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Versatile routes for synthesis of diarylamines through acceptorless dehydrogenative aromatization catalysis over supported gold-palladium bimetallic nanoparticles2017

    • Author(s)
      Taniguchi, K.; Jin, X.; Yamaguchi, K.; Nozaki, K.; Mizuno, N.
    • Journal Title

      Chem. Sci.

      Volume: 8 Issue: 3 Pages: 2131-2142

    • DOI

      10.1039/c6sc04455g

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Gold nanoparticles on OMS-2 for heterogeneously catalyzed aerobic oxidative α,β-dehydrogenation of β-heteroatom-substituted ketones2016

    • Author(s)
      Yoshii, D.; Jin, X.; Yatabe, T.; Hasegawa, J.; Yamaguchi, K.; Mizuno, N.
    • Journal Title

      Chem. Commun.

      Volume: 52 Issue: 99 Pages: 14314-14317

    • DOI

      10.1039/c6cc07846j

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Au-Pd alloy nanoparticles supported on layered double hydroxide for heterogeneously catalyzed aerobic oxidative dehydrogenation of cyclohexanols and cyclohexanones to phenols2016

    • Author(s)
      Jin, X.; Taniguchi, K.; Yamaguchi, K.; Mizuno, N.
    • Journal Title

      Chem. Sci.

      Volume: 7 Issue: 8 Pages: 5371-5383

    • DOI

      10.1039/c6sc00874g

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Supported Gold Nanoparticles for Efficient α-Oxygenation of Secondary and Tertiary Amines into Amides2016

    • Author(s)
      Jin, X.; Kataoka, K.; Yatabe, T.; Yamaguchi, K.; Mizuno, N.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 25 Pages: 7212-7217

    • DOI

      10.1002/anie.201602695

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of N-Acylsulfenamides through Aerobic Cross Dehydrogenative Coupling of Thiols and Amides by Supported Copper Hydroxide Catalyst2016

    • Author(s)
      K. Sakagami, X. Jin, K. Suzuki, K. Yamaguchi, N. Mizuno
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 2 Pages: 173-175

    • DOI

      10.1246/cl.151090

    • NAID

      130005124734

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Facile Access to N-Substituted Anilines via Dehydrogenative Aromatization Catalysis over Supported Gold-palladium Bimetallic Nanoparticles2016

    • Author(s)
      K. Taniguchi, X. Jin, K. Yamaguchi, N. Mizuno
    • Journal Title

      Catal. Sci. Technol.

      Volume: 6 Issue: 11 Pages: 3929-3937

    • DOI

      10.1039/c5cy01908g

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Supported gold-palladium alloy nanoparticles catalyzed tandem oxidation routes to N-substituted anilines from non-aromatic compounds2015

    • Author(s)
      K. Taniguchi, X. Jin, K. Yamaguchi, N. Mizuno
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 81 Pages: 14969-14972

    • DOI

      10.1039/c5cc06514c

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Gold Nanoparticles Supported on a Layered Double Hydroxide as Efficient Catalysts for the One-Pot Synthesis of Flavones2015

    • Author(s)
      T. Yatabe, X. Jin, K. Yamaguchi, N. Mizuno
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 54 Issue: 45 Pages: 13302-13306

    • DOI

      10.1002/anie.201507134

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Ni-Mg-Al層状複合水酸化物担持Pd触媒による高効率アクセプターレス脱水素芳香環形成反応2017

    • Author(s)
      金 雄傑・山口 和也・水野 哲孝
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス(神奈川県横浜市港北区)
    • Related Report
      2016 Annual Research Report
  • [Presentation] OMS-2担持金ナノ粒子触媒による酸素を酸化剤としたβ-ヘテロ原子置換飽和ケトンのα,β-脱水素反応2017

    • Author(s)
      吉井 大地・谷田部 孝文・金 雄傑・山口 和也・水野 哲孝
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス(神奈川県横浜市港北区)
    • Related Report
      2016 Annual Research Report
  • [Presentation] 銅触媒によるアルコールを用いたアミドの酸化的アシル化反応2017

    • Author(s)
      片岡 憲吾・金 雄傑・山口 和也・水野 哲孝
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス(神奈川県横浜市港北区)
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis of Diarylamines through Supported Gold-Palladium Nanoparticles-Catalyzed Acceptorless Dehydrogenative Aromatization2017

    • Author(s)
      K. Taniguchi, X. Jin, K. Yamaguchi, K. Nozaki, N. Mizuno
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス(神奈川県横浜市港北区)
    • Related Report
      2016 Annual Research Report
  • [Presentation] 担持パラジウムナノ粒子触媒によるアンモニアのアリール化反応2017

    • Author(s)
      小泉 悠・谷口 健人・金 雄傑・山口 和也・水野 哲孝
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス(神奈川県横浜市港北区)
    • Related Report
      2016 Annual Research Report
  • [Presentation] 酸化的脱水素反応を鍵反応とした環境調和型フラボン類One-Pot合成の開発2016

    • Author(s)
      谷田部 孝文・ 金 雄傑・山口 和也・水野 哲孝
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市多々羅都谷)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Au-Pd合金ナノ粒子触媒による空気を酸化剤とした シクロヘキサノールのフェノールへの脱水素型酸化反応2016

    • Author(s)
      金 雄傑・山口 和也・水野 哲孝
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市多々羅都谷)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 担持金ナノ粒子触媒による酸素を酸化剤とした飽和ケトンのα,β-不飽和ケトンへの酸化的脱水素反応2016

    • Author(s)
      吉井 大地・谷田部 孝文・金 雄傑・山口 和也・水野 哲孝
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市多々羅都谷)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 担持金-パラジウムナノ粒子触媒を用いたタンデム型脱水素芳香環形成反応によるN-置換アニリン合成2016

    • Author(s)
      谷口健人・金雄傑・山口和也・水野哲孝
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市多々羅都谷)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 担持金ナノ粒子触媒による酸素を酸化剤としたアミンの形式的α-酸素化反応2016

    • Author(s)
      片岡 憲吾・金 雄傑・山口 和也・水野 哲孝
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市多々羅都谷)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Environmentally-Friendly Heterogeneous One-Pot Synthesis of Flavones through the Concerted Catalysis of Gold Nanoparticles Supported on Layered Double Hydroxides2016

    • Author(s)
      T. Yatabe, X. Jin, K. Yamaguchi, N. Mizuno,
    • Organizer
      The 6th Asia-Oceania Conference on Sustainable and Green Chemistry
    • Place of Presentation
      Hongkong (China)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 担持金ナノ粒子触媒による酸素を酸化剤としたアミンのα-酸素化反応2016

    • Author(s)
      片岡 憲吾・金 雄傑・山口 和也・水野 哲孝
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Related Report
      2016 Annual Research Report
  • [Presentation] 担持Au-Pd合金ナノ粒子触媒によるシクロヘキサノール及びシクロヘキサノンのフェノールへの脱水素型酸化反応2016

    • Author(s)
      金 雄傑・山口 和也・水野 哲孝
    • Organizer
      第49回酸化反応討論会
    • Place of Presentation
      徳島大学常三島キャンパス(徳島県徳島市南常三島町)
    • Related Report
      2016 Annual Research Report
  • [Presentation] モリブドバナドリン酸を触媒としたチオアミドの脱硫-酸素化反応2016

    • Author(s)
      山口 和也・徐 寧・金 雄傑・鈴木 康介・水野 哲孝
    • Organizer
      第118回触媒討論会
    • Place of Presentation
      岩手大学(岩手県盛岡市上田)
    • Related Report
      2016 Annual Research Report
  • [Presentation] 担持金ナノ粒子触媒による酸素を酸化剤としたアミンのα-酸素化反応2016

    • Author(s)
      片岡 憲吾・金 雄傑・山口 和也・水野 哲孝
    • Organizer
      第118回触媒討論会
    • Place of Presentation
      岩手大学(岩手県盛岡市上田)
    • Related Report
      2016 Annual Research Report
  • [Presentation] Aerobic Oxidative Dehydrogenation of Cyclohexanols to Phenols by Layered Double Hydroxide Supported Au-Pd Alloy Nanoparticles2016

    • Author(s)
      X. Jin, K. Yamaguchi, N. Mizuno
    • Organizer
      The 16th International Congress on Catalysis
    • Place of Presentation
      Beijing (China)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Supported Au-Pd Alloy Nanoparticles Catalyzed Tandem Oxidative Aromatization for Synthesis of N-Substituted Anilines2016

    • Author(s)
      K. Taniguchi, X. Jin, K. Yamaguchi, N. Mizuno
    • Organizer
      The 16th International Congress on Catalysis
    • Place of Presentation
      Beijing (China)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Au/LDH触媒の協奏的触媒作用を利用した環境調和型フラボン類One-Pot合成2016

    • Author(s)
      谷田部 孝文・金 雄傑・山口 和也・水野 哲孝
    • Organizer
      第5回JACI/GSCシンポジウム
    • Place of Presentation
      ANAクラウンプラザホテル神戸(兵庫県神戸市中央区)
    • Related Report
      2016 Annual Research Report
  • [Remarks] 水野・山口研究室ホームページ

    • URL

      http://park.itc.u-tokyo.ac.jp/mizuno/japanese/

    • Related Report
      2016 Annual Research Report

URL: 

Published: 2015-08-26   Modified: 2018-03-22  

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