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Development of high-performance multinuclear catalysts for environmentally-benign cross-coupling reactions

Research Project

Project/Area Number 18K14057
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 27030:Catalyst and resource chemical process-related
Research InstitutionHokkaido University

Principal Investigator

Maeno Zen  北海道大学, 触媒科学研究所, 特任講師 (30721154)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Discontinued (Fiscal Year 2020)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2020: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsクロスカップリング反応 / リン酸アルミニウム / 分子状酸素 / カテコール / 求核剤 / 脱水素型クロスカップリング / 多核金属触媒 / 選択酸化 / C-H活性化 / ルテニウム / ロジウム / 脱水素クロスカップリング / フェノール類 / オルトキノン
Outline of Final Research Achievements

In this study, we have developed immobilized catalysts that promote the cross-coupling reaction of catechol with active methylene compounds. Although this reaction is useful for the total synthesis of biologically active compounds, it has been limited to stoichiometric and enzymatic reactions, and there have been no examples of heterogenous catalyst systems using O2 as an oxidant. As a result of our investigations, we found that aluminum phosphate (AlPO4) immobilized metal catalysts can promote several cross-coupling reaction in a highly selective manner. The developed catalytic system was applicable to the synthesis of catechol derivatives, which are useful for the total synthesis of various bioactive substances.

Academic Significance and Societal Importance of the Research Achievements

酸化的脱水素カップリング反応は、基質のC-H結合から新たな結合を直接形成でき、基質の予備官能基化を必要としない次世代型の分子変換反応である。特に、O2を酸化剤(水素アクセプター)とするカップリング反応は、環境に負担のない水のみを副生成物とするため、シンプルかつクリーンな分子変換法となりうる。本成果は、環境調和型分子変換法及びそのための触媒設計指針の提示につながるので、有機化学と触媒化学の両方の発展に貢献できる。

Report

(3 results)
  • 2020 Final Research Report ( PDF )
  • 2019 Annual Research Report
  • 2018 Research-status Report
  • Research Products

    (25 results)

All 2020 2019 2018 Other

All Journal Article (18 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 18 results,  Open Access: 3 results) Presentation (6 results) (of which Int'l Joint Research: 2 results,  Invited: 3 results) Remarks (1 results)

  • [Journal Article] A CHA zeolite supported Ga-oxo cluster for partial oxidation of CH4 at room temperature2020

    • Author(s)
      Yasumura Shunsaku、Huang Mengwen、Wu Xiaopeng、Liu Chong、Toyao Takashi、Maeno Zen、Shimizu Ken-ichi
    • Journal Title

      Catalysis Today

      Volume: 352 Pages: 118-126

    • DOI

      10.1016/j.cattod.2019.10.035

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formation and Reactions of NH4NO3 during Transient and Steady-State NH3-SCR of NOx over H-AFX Zeolites: Spectroscopic and Theoretical Studies2020

    • Author(s)
      Kubota Hiroe、Liu Chong、Toyao Takashi、Maeno Zen、Ogura Masaru、Nakazawa Naoto、Inagaki Satoshi、Kubota Yoshihiro、Shimizu Ken-ichi
    • Journal Title

      ACS Catalysis

      Volume: 10 Issue: 3 Pages: 2334-2344

    • DOI

      10.1021/acscatal.9b05151

    • NAID

      120006957265

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Methylation of Aromatic Hydrocarbons using CO2/H2 over Re/TiO2 and H‐MOR Catalysts2020

    • Author(s)
      Ting Kah Wei、Kamakura Haruka、Poly Sharmin S.、Toyao Takashi、Hakim Siddiki S. M. A.、Maeno Zen、Matsushita Koichi、Shimizu Ken‐ichi
    • Journal Title

      ChemCatChem

      Volume: 12 Issue: 8 Pages: 2215-2220

    • DOI

      10.1002/cctc.202000036

    • NAID

      120007026929

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Isolated Indium Hydrides in CHA Zeolites: Speciation and Catalysis for Nonoxidative Dehydrogenation of Ethane2020

    • Author(s)
      Maeno Zen、Yasumura Shunsaku、Wu Xiaopeng、Huang Mengwen、Liu Chong、Toyao Takashi、Shimizu Ken-ichi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 10 Pages: 4820-4832

    • DOI

      10.1021/jacs.9b13865

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] High-silica Hβ zeolite catalyzed methanolysis of triglycerides to form fatty acid methyl esters (FAMEs)2020

    • Author(s)
      Jamil Md.A.R.、Touchy Abeda Sultana、Poly Sharmin Sultana、Rashed Md. Nurnobi、Siddiki S.M.A. Hakim、Toyao Takashi、Maeno Zen、Shimizu Ken-ichi
    • Journal Title

      Fuel Processing Technology

      Volume: 197 Pages: 106204-106204

    • DOI

      10.1016/j.fuproc.2019.106204

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] N-Methylation of Amines and Nitroarenes with Methanol Using Heterogeneous Platinum Catalysts2019

    • Author(s)
      Md. A. R. Jamil, A. S. Touchy, Md. N. Rashed, K. W. Ting, SMA. H. Siddiki, T. Toyao, Z. Maeno, K. Shimizu
    • Journal Title

      J. Catal.

      Volume: 371 Pages: 47-56

    • DOI

      10.1016/j.jcat.2019.01.027

    • Related Report
      2019 Annual Research Report 2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Experimental and theoretical study of multinuclear indium-oxo clusters in CHA zeolite for CH4 activation at room temperature2019

    • Author(s)
      Maeno Zen、Yasumura Shunsaku、Liu Chong、Toyao Takashi、Kon Kenichi、Nakayama Akira、Hasegawa Jun-ya、Shimizu Ken-ichi
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 21 Issue: 25 Pages: 13415-13427

    • DOI

      10.1039/c9cp01873e

    • NAID

      120006866524

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Phenolysis Reactions of Unactivated Amides into Phenolic Esters Promoted by a Heterogeneous CeO 2 Catalyst2019

    • Author(s)
      Rashed Md. Nurnobi、Siddiki S. M. A. Hakim、Touchy Abeda Sultana、Jamil Md. A. R.、Poly Sharmin Sultana、Toyao Takashi、Maeno Zen、Shimizu Ken‐ichi
    • Journal Title

      Chemistry A European Journal

      Volume: 25 Issue: 45 Pages: 10594-10605

    • DOI

      10.1002/chem.201901446

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Heterogeneous Pt and MoOx Co-Loaded TiO2 Catalysts for Low-Temperature CO2 Hydrogenation To form CH3OH2019

    • Author(s)
      Takashi Toyao, Shingo Kayamori, Zen Maeno, S. M. A. Hakim Siddiki, and Ken-ichi Shimizu
    • Journal Title

      ACS Catal. 2019

      Volume: 9 Issue: 9 Pages: 8187-8196

    • DOI

      10.1021/acscatal.9b01225

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Acetalization of glycerol with ketones and aldehydes catalyzed by high silica Hβ zeolite2019

    • Author(s)
      Poly Sharmin Sultana、Jamil Md.A.R.、Touchy Abeda S.、Yasumura Shunsaku、Siddiki S.M.A. Hakim、Toyao Takashi、Maeno Zen、Shimizu Ken-ichi
    • Journal Title

      Molecular Catalysis

      Volume: 479 Pages: 110608-110608

    • DOI

      10.1016/j.mcat.2019.110608

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Mechanistic study of the selective hydrogenation of carboxylic acid derivatives over supported rhenium catalysts2019

    • Author(s)
      Takashi Toyao, Kah Wei Ting, S. M. A. Hakim Siddiki, Abeda S. Touchy, Wataru Onodera, Zen Maeno, Hiroko Ariga-Miwa, Yasuharu Kanda, Kiyotaka Asakura and Ken-ichi Shimizu
    • Journal Title

      Catal. Sci. Technol.

      Volume: 9 Issue: 19 Pages: 5413-5424

    • DOI

      10.1039/c9cy01404g

    • NAID

      120006890338

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Statistical Analysis and Discovery of Heterogeneous Catalysts Based on Machine Learning from Diverse Published Data2019

    • Author(s)
      Suzuki Keisuke、Toyao Takashi、Maeno Zen、Takakusagi Satoru、Shimizu Ken‐ichi、Takigawa Ichigaku
    • Journal Title

      ChemCatChem

      Volume: 11 Issue: 18 Pages: 4537-4547

    • DOI

      10.1002/cctc.201900971

    • NAID

      120006866531

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient synthesis of benzofurans via cross-coupling of catechols with hydroxycoumarins using O2 as an oxidant catalyzed by AlPO4-supported Rh nanoparticle2019

    • Author(s)
      Z. Maeno, M. Yamamoto, T. Mitsudome, T. Mizugaki, K. Jitsukawa
    • Journal Title

      ChemistrySelect

      Volume: 4 Issue: 38 Pages: 11394-11397

    • DOI

      10.1002/slct.201903117

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Promotional Effect of La in the Three-Way Catalysis of La-Loaded Al2O3-Supported Pd Catalysts (Pd/La/Al2O3)2019

    • Author(s)
      Jing Yuan、Cai Zhengxu、Liu Chong、Toyao Takashi、Maeno Zen、Asakura Hiroyuki、Hiwasa Satoru、Nagaoka Shuhei、Kondoh Hiroshi、Shimizu Ken-ichi
    • Journal Title

      ACS Catalysis

      Volume: 10 Issue: 2 Pages: 1010-1023

    • DOI

      10.1021/acscatal.9b03766

    • NAID

      120006953324

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Oxidative cross-coupling reaction of catechols with active methylene compounds in an aqueous medium using an AlPO4-supported Ru catalyst2018

    • Author(s)
      Maeno Zen、Yamamoto Masanobu、Mitsudome Takato、Mizugaki Tomoo、Jitsukawa Koichiro
    • Journal Title

      Catalysis Science & Technology

      Volume: 8 Issue: 21 Pages: 5401-5405

    • DOI

      10.1039/c8cy01425f

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Esterification of Tertiary Amides by Alcohols Through C-N Bond Cleavage over CeO22018

    • Author(s)
      Toyao Takashi、Nurnobi?Rashed Md.、Morita Yoshitsugu、Kamachi Takashi、Hakim?Siddiki S. M. A.、Ali Md. A.、Touchy A. S.、Kon Kenichi、Maeno Zen、Yoshizawa Kazunari、Shimizu Ken-ichi
    • Journal Title

      ChemCatChem

      Volume: 11 Issue: 1 Pages: 449-456

    • DOI

      10.1002/cctc.201801098

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Acceptorless Dehydrogenative Synthesis of Pyrimidines from Alcohols and Amidines Catalyzed by Supported Platinum Nanoparticles2018

    • Author(s)
      Sultana Poly Sharmin、Siddiki S. M. A. Hakim、Touchy Abeda S.、Ting Kah Wei、Toyao Takashi、Maeno Zen、Kanda Yasuharu、Shimizu Ken-ichi
    • Journal Title

      ACS Catalysis

      Volume: 8 Issue: 12 Pages: 11330-11341

    • DOI

      10.1021/acscatal.8b02814

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] High-silica Hβ zeolites for catalytic hydration of hydrophobic epoxides and alkynes in water2018

    • Author(s)
      Sultana Poly Sharmin、Hakim Siddiki S.M.A.、Touchy Abeda S.、Yasumura Shunsaku、Toyao Takashi、Maeno Zen、Shimizu Ken-ichi
    • Journal Title

      Journal of Catalysis

      Volume: 368 Pages: 145-154

    • DOI

      10.1016/j.jcat.2018.10.004

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Heterogeneously-catalyzed Dehydrogenative Coupling Reactions of Phenolic Compounds Using O2 as Green Oxidant2019

    • Author(s)
      Zen Maeno
    • Organizer
      World Chemistry Forum 2019
    • Related Report
      2019 Annual Research Report 2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ゼオライト固定化インジウム酸素クラスターの合成とメタン活性化能2019

    • Author(s)
      前野禅、安村駿作、Liu Chong、鳥屋尾隆、今健一、中山哲、長谷川淳也、清水研一
    • Organizer
      第124回触媒討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] インジウム交換CHAゼオライト内で生成するヒドリド種の構造と脱水素触媒作用2019

    • Author(s)
      前野禅、安村駿作、Wu Xiaopeng、Liu Chong、鳥屋尾隆、清水研一
    • Organizer
      第125回触媒討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 規則性有機・無機ナノ空間を反応場とする金属触媒開発と環境調和型反応2018

    • Author(s)
      前野 禅
    • Organizer
      第56回触媒研究懇談会
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] 環境調和型酸化的カップリング反応 を促進する固定化金属ナノ粒子触媒2018

    • Author(s)
      前野 禅
    • Organizer
      ナノ構造触媒研究会青森講演会
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] Aerobic Oxidative Cross-Coupling Reaction of Catehols and Active Methylene Compounds Using Supported Metal Catalysts2018

    • Author(s)
      Zen Maeno, Masanobu Yamamoto, Takato Mitsudome, Tomoo Mizugaki, Koichiro Jitsukawa
    • Organizer
      The 8th Tokyo Conference on Advanced Catalytic Science and Technology
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Remarks] プレスリリース インジウムヒドリドの優れた脱水素触媒作用を発見

    • URL

      https://www.hokudai.ac.jp/news/200306_pr.pdf

    • Related Report
      2019 Annual Research Report

URL: 

Published: 2018-04-23   Modified: 2022-01-27  

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