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2011 Fiscal Year Final Research Report

Development of polymer immobilized metal nanocluster catalysts toward efficient one-pot tandem synthetic reactions

Research Project

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Project/Area Number 22750032
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

MIYAMURA Hiroyuki  東京大学, 大学院・理学系研究科, 特任助教 (00548943)

Project Period (FY) 2010 – 2011
Keywords固相触媒 / 金 / ワンポット反応 / エステル / アミド / 酸素酸化 / ナノクラスター
Research Abstract

We have already developed gold nanocluster and bimetallic cluster catalysts immobilized on polystyrene-based polymer(PI-Au, PI-Au/M) and on carbon black-stabilized polymer(PI/CB-Au, PI/CB-Au/M), and found that these catalysts mediated aerobic oxidation of alcohols and so on. In this research, we have newly developed direct oxidative ester formation reactions from alcohols and one-pot aerobic oxidation-Michael reaction between allylic alcohols and 1, 3-dicarbonyl compounds. We have also realized aerobic oxidative amidation reaction from alcohols and amines using newly developed bimetallic catalysts of gold and iron-group metals(PI/CB-Au/Ni,-Au/Co,-Au/Fe). In addition, we have developed oxidative benzoxazole and benzothiazole synthesis from Schiff bases composed of o-aminophenols and aldehydes. These heterocycles could be obtained from N-alkyl-o-aminophenols through three step reactions including two aerobic oxidation steps in one-pot.

  • Research Products

    (15 results)

All 2012 2011 2010

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Oxidative transformation of N-sustituted2-aminophenols to 2-substitutedbenzoxazoles catalyzed bypolymer-incarcerated, carbon-stabilizedplatinum nanoclusters2012

    • Author(s)
      Yoo, Woo-Jin ; Yuan, Hao ; Miyamura, Hiroyuki ; Kobayashi, Shu
    • Journal Title

      Can. J. Chem

      Volume: 90 Pages: 306-313

    • DOI

      doi:10.1139/v11-161

    • Peer Reviewed
  • [Journal Article] Multiphase Flow Systems for Selective Aerobic Oxidation of Alcohols Catalyzed by Bimetallic Nanoclusters2012

    • Author(s)
      Kaizuka, Kosuke ; Lee, Ka-Young ; Miyamura, Hiroyuki ; Kobayashi, Sh.
    • Journal Title

      J. Flow Chem

      Volume: 2 Pages: 1-4

    • DOI

      doi:10.1556/jfchem.2011.00014

    • Peer Reviewed
  • [Journal Article] Facile Preparation of 2-Substituted Benzoxazoles and Benzothiazoles via AerobicOxidation of Phenolic and Thiophenolic Imines Catalyzed by Polymer-Incarcerated Platinum Nanoclusters2011

    • Author(s)
      Yoo, Woo-Jin ; Yuan, Hao ; Miyamura, Hiroyuki ; Kobayashi, Sh.
    • Journal Title

      Adv. Synth. Catal

      Volume: 353(17) Pages: 3085-3089

    • DOI

      doi:10.1002/adsc.201100430

    • Peer Reviewed
  • [Journal Article] Copper-catalyzed, aerobic oxidative cross-coupling of alkynes with arylboronic acids : remarkable selectivity in 2, 6-lutidine media2011

    • Author(s)
      Yasukawa, Tomohiro ; Miyamura, Hiroyuki ; Kobayashi, Sh.
    • Journal Title

      Org. Biomol. Chem

      Volume: 9(18) Pages: 6208-6210

    • DOI

      doi:10.1039/c1ob05915g

    • Peer Reviewed
  • [Journal Article] Powerful Amide Synthesis from Alcoholsand Amines under Aerobic Conditions Catalyzed by Gold or Gold/Iron,-Nickel or-Cobalt Nanoparticles2011

    • Author(s)
      Soule, Jean-Francois ; Miyamura, Hiroyuki ; Kobayashi, Shu.
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133(46) Pages: 18550-18553

    • DOI

      doi:10.1021/ja2080086

    • Peer Reviewed
  • [Journal Article] Aerobic Oxidation of Amines Catalyzed by Polymer-Incarcerated Au Nanoclusters : Effect of Cluster Size and Cooperative Functional Groups in the Polymer2011

    • Author(s)
      Miyamura, Hiroyuki ; Morita, Masataka ; Inasaki, Takeshi ; Kobayashi, Shu
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 84(6) Pages: 588-599

    • DOI

      doi:10.1246/bcsj.20100300

    • Peer Reviewed
  • [Journal Article] Polymer-Incarcerated Gold-Palladium Nanoclusters with Boron on Carbon : A Mild and Efficient Catalyst for the Sequential Aerobic Oxidation-Michael Addition of 1, 3-Dicarbonyl Compounds to Allylic Alcohols2011

    • Author(s)
      Yoo, Woo-Jin ; Miyamura, Hiroyuki ; Kobayashi, Shu
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133(9) Pages: 3095-3103

    • DOI

      doi:10.1021/ja110142y

    • Peer Reviewed
  • [Journal Article] Rate-Acceleration in Gold-Nanocluster-Catalyzed Aerobic Oxidative Esterification Using 1, 2-and1, 3-Diols and Their Derivatives2011

    • Author(s)
      Yasukawa, Tomohiro ; Miyamura, Hiroyuki ; Kobayashi, Shu
    • Journal Title

      Chem. Asian J

      Volume: 6(2) Pages: 621-627

    • DOI

      doi:10.1002/asia.201000624

    • Peer Reviewed
  • [Journal Article] In situ coupled oxidation cycle catalyzed by highly active and reusable Pt-catalysts : dehydrogenative oxidation reactions in the presence of a catalytic amount of o-chloranil using molecular oxygen as the terminal oxidant2010

    • Author(s)
      Miyamura, Hiroyuki ; Maehata, Kanako ; Kobayashi, Shu
    • Journal Title

      Chem. Commun

      Volume: 46(42) Pages: 8052-8054

    • DOI

      doi:10.1039/c0cc02865g

    • Peer Reviewed
  • [Journal Article] Remarkable Effect of Bimetallic Nanocluster Catalysts for Aerobic Oxidation of Alcohols : Combining Metals Changes the Activities and the Reaction Pathways to Aldehydes/Carboxylic Acids or Esters2010

    • Author(s)
      Kaizuka, Kosuke ; Miyamura, Hiroyuki ; Kobayashi, Shu
    • Journal Title

      J. Am. Chem. Soc

      Volume: 132(43) Pages: 15096-15098

    • DOI

      doi:10.1021/ja108256h

    • Peer Reviewed
  • [Journal Article] Enhanced acyl radical formation in the Au nanoparticle-catalysed aldehyde oxidation2010

    • Author(s)
      Conte, Marco ; Miyamura, Hiroyuki ; Kobayashi, Sh.; Chechik, Victor
    • Journal Title

      Chem. Commun

      Volume: 46(1) Pages: 145-147

    • DOI

      doi:10.1039/b918200d

    • Peer Reviewed
  • [Journal Article] Aerobic oxidative esterification of alcohols catalyzed by polymer-incarcerated gold nanoclusters under ambient conditions2010

    • Author(s)
      Miyamura, Hiroyuki ; Yasukawa, Tomohiro ; Kobayashi, Shu
    • Journal Title

      Green Chem

      Volume: 12(5) Pages: 776-778

    • DOI

      doi:10.1039/b926877d

    • Peer Reviewed
  • [Presentation] Aerobic Oxidation of Amines Catalyzed by Polymer Incarcerated Gold Nanocluster : Effect of Cluster Size and Functionality in Polymer2011

    • Author(s)
      Miyamura, Hiroyuki ; Morita, Masataka.; Kobayashi, Sh.
    • Organizer
      The 7th International Symposium on Intergrated Synthesis(ISIS-7)
    • Place of Presentation
      Maiko Villa Kobe, Kobe, Japan
    • Year and Date
      20111009-10
  • [Presentation] Environmentally Benign Oxidations Catalyzed by Polymer Incarcerated Metal Cluster Catalysts2010

    • Author(s)
      Miyamura, Hiroyuki
    • Organizer
      The Reaxys^[○! R] PhD Prize Symposium, 3^<rd> EuCheMS Chemistry Congress Nurnberg
    • Place of Presentation
      Nurnberg, Germany
    • Year and Date
      20100829-0902
  • [Patent(Industrial Property Rights)] アミド化合物の製造方法とその触媒2011

    • Inventor(s)
      小林修、宮村浩之、Soule, Jean-Francois
    • Industrial Property Rights Holder
      国立大学法人東京大学、JX日鉱日石エネルギー株式会社
    • Industrial Property Number
      特願、2011-206366
    • Filing Date
      2011-09-21

URL: 

Published: 2013-07-31  

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