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Hydration of organic compounds catalyzed by metal porphyrins

Research Project

Project/Area Number 23750109
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

NAKA Hiroshi  名古屋大学, 物質科学国際研究センター, 助教 (70431517)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords錯体 / 有機金属触媒 / 反応有機化学 / 水和反応 / ポルフィリン / 分子触媒 / 錯体・有機金属触媒
Research Abstract

We have developed water-soluble cobalt(III) porphyrin complexes that promote the hydration of terminal alkynes to produce methyl ketones. The alkyne hydration was compatible with the presence of acid/base- or redox-sensitive functional groups such as alkyl silyl ethers; allyl ethers; trityl ethers; benzyl ethers; carboxylic esters; boronic esters; carboxamides; nitriles; and acetal groups. Some of the alkyne substrates tested here are otherwise difficult to hydrate. The reaction mechanism was also clarified using spectroscopic, kinetic, and theoretical methods.

Report

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

    (34 results)

All 2013 2012 2011 Other

All Journal Article (2 results) (of which Peer Reviewed: 1 results) Presentation (28 results) Remarks (4 results)

  • [Journal Article] Hydration of Terminal Alkynes Catalyzed by Water-Soluble Cobalt Porphyrin Complexes2013

    • Author(s)
      Tadashi Tachinami, Takuho Nishimura, Richiro Ushimaru, Ryoji Noyori, and Hiroshi Naka
    • Journal Title

      J. Am. Chem. Soc

      Volume: 135 Pages: 50-53

    • Related Report
      2012 Final Research Report
  • [Journal Article] Hydration of Terminal Alkynes Catalyzed by Water-Soluble Cobalt Porphyrin Complexes2013

    • Author(s)
      Tadashi Tachinami, Takuho Nishimura, Richiro Ushimaru, Ryoji Noyori, and Hiroshi Naka,
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 1 Pages: 50-53

    • DOI

      10.1021/ja310282t

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] 水溶性コバルト(III)ポルフィリン触媒による末端アルキンの水和反応2013

    • Author(s)
      西村 拓歩・立浪 忠志・牛丸 理一郎・野依 良治・中 寛史
    • Organizer
      日本化学会第93春季年会 2F6-46
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス,滋賀(口頭)
    • Related Report
      2012 Final Research Report
  • [Presentation] コバルト(III)ポルフィリン錯体による末端アルキンの触媒的活性化2013

    • Author(s)
      牛丸 理一郎・野依 良治・中 寛史
    • Organizer
      日本化学会第93春季年会 2F6-47
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス,滋賀(口頭)
    • Related Report
      2012 Final Research Report
  • [Presentation] 水溶性コバルト(III)ポルフィリン触媒による末端アルキンの水和反応2013

    • Author(s)
      西村 拓歩・立浪 忠志・牛丸 理一郎・野依 良治・中 寛史
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学,滋賀
    • Related Report
      2012 Annual Research Report
  • [Presentation] コバルト(III)ポルフィリン錯体による末端アルキンの触媒的活性化2013

    • Author(s)
      牛丸 理一郎・野依 良治・中 寛史
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学,滋賀
    • Related Report
      2012 Annual Research Report
  • [Presentation] Hydration of Terminal Alkynes to Methyl Ketones Catalyzed by Water-Soluble Cobalt(III) Porphyrin Complexes2013

    • Author(s)
      Hiroshi Naka, Takuho Nishimura, Tadashi Tachinami, Richiro Ushimaru, Ryoji Noyori
    • Organizer
      10th Congress on Catalysis Applied to Fine Chemicals
    • Place of Presentation
      Turku, Finland
    • Related Report
      2012 Annual Research Report
  • [Presentation] DFT Studies on Cobalt-Catalyzed Addition of Methanol to Terminal Alkynes: Alkynophilic Cobalt(III) Porphyrin Complexes2012

    • Author(s)
      Richrio Ushimaru, Ryoji Noyori, and Hiroshi Naka
    • Organizer
      The 2nd International Conference on MEXT Project of Integrated Research on Chemical Synthesis
    • Place of Presentation
      Nagoya (poster)
    • Related Report
      2012 Final Research Report
  • [Presentation] Cobalt-catalyzed Markovnikov Functionalization of Terminal Alkynes2012

    • Author(s)
      Hiroshi Naka, Tadashi Tachinami, Richiro Ushimaru, Takuho Nishimura, Ryoji Noyori
    • Organizer
      International Conference "Catalysis in Organic Synthesis" (ICCOS-2012), #OC25
    • Place of Presentation
      Moscow, Russia (oral)
    • Related Report
      2012 Final Research Report
  • [Presentation] Chemoselective Hydration of Terminal Alkynes Catalyzed by Cobalt(III) porphyrin Complex2012

    • Author(s)
      Takuho Nishimura, Tadashi Tachinami, Richiro Ushimaru, Ryoji Noyori, Hiroshi Naka
    • Organizer
      International Conference "Catalysis in Organic Synthesis" (ICCOS-2012), #P185
    • Place of Presentation
      Moscow, Russia (poster).
    • Related Report
      2012 Final Research Report
  • [Presentation] コバルト触媒を用いた末端アルキンの水和反応の反応機構2012

    • Author(s)
      牛丸 理一郎,立浪 忠志,西村 拓歩,野依 良治,中 寛史
    • Organizer
      第3回統合物質シンポジウム「新エネルギーと物質創製」
    • Place of Presentation
      福岡(ポスター)
    • Related Report
      2012 Final Research Report
  • [Presentation] コバルト触媒を用いた末端アルキンに対するメタノールの二重付加反応についての速度論的研究2012

    • Author(s)
      牛丸 理一郎,立浪 忠志,西村 拓歩,野依 良治,中 寛史
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉,神奈川
    • Related Report
      2012 Final Research Report
  • [Presentation] DFT Studies on Cobalt-Catalyzed Addition of Methanol to Terminal Alkynes: Alkynophilic Cobalt(III) Porphyrin Complexes2012

    • Author(s)
      Richrio Ushimaru, Ryoji Noyori, and Hiroshi Naka
    • Organizer
      The 2nd International Conference on MEXT Project of Integrated Research on Chemical Synthesis
    • Place of Presentation
      Nagoya
    • Related Report
      2012 Annual Research Report
  • [Presentation] Cobalt-catalyzed Markovnikov Functionalization of Terminal Alkynes2012

    • Author(s)
      Hiroshi Naka, Tadashi Tachinami, Richiro Ushimaru, Takuho Nishimura, Ryoji Noyori
    • Organizer
      International Conference “Catalysis in Organic Synthesis” (ICCOS-2012)
    • Place of Presentation
      Moscow, Russia
    • Related Report
      2012 Annual Research Report
  • [Presentation] Chemoselective Hydration of Terminal Alkynes Catalyzed by Cobalt(III) porphyrin Complex2012

    • Author(s)
      Takuho Nishimura, Tadashi Tachinami, Richiro Ushimaru, Ryoji Noyori, Hiroshi Naka
    • Organizer
      International Conference “Catalysis in Organic Synthesis” (ICCOS-2012)
    • Place of Presentation
      Moscow, Russia
    • Related Report
      2012 Annual Research Report
  • [Presentation] コバルト触媒を用いた末端アルキンの水和反応の反応機構2012

    • Author(s)
      牛丸 理一郎,立浪 忠志,西村 拓歩,野依 良治,中 寛史
    • Organizer
      第3回統合物質シンポジウム「新エネルギーと物質創製」
    • Place of Presentation
      福岡
    • Related Report
      2012 Annual Research Report
  • [Presentation] コバルト触媒を用いた末端アルキンに対 するメタノールの二重付加反応について の速度論的研究2012

    • Author(s)
      牛丸理一郎・立浪忠志・西村拓歩・野依良治・中 寛 史
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      日吉、神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] Kinetic studies on the Cobalt-Catalyzed Double Addition of Methanol to Terminal Alkynes2011

    • Author(s)
      Richiro Ushimaru, Tadashi Tachinami, Ryoji Noyori, and Hiroshi Naka
    • Organizer
      第4回グローバルCOE 化学 成果報告会
    • Place of Presentation
      名古屋(ポスター)
    • Year and Date
      2011-06-15
    • Related Report
      2012 Final Research Report
  • [Presentation] Mechanistic Insights into the Double Addition of Methanol to Terminal Alkynes Catalyzed by Cobalt complexes2011

    • Author(s)
      Richiro Ushimaru, Tadashi Tachinami, Takuho Nishimura, Ryoji Noyori, and Hiroshi Naka
    • Organizer
      7thand 8thYoshimasa Hirata Memorial Lecture
    • Place of Presentation
      Nagoya (poster)
    • Related Report
      2012 Final Research Report
  • [Presentation] Mechanistic Insights into the Cobalt-Catalyzed Double Addition of Methanol to Terminal Alkynes2011

    • Author(s)
      Richiro Ushimaru, Tadashi Tachinami, Takuho Nishimura, Ryoji Noyori, and Hiroshi Naka
    • Organizer
      12thIRTG Joint Symposium
    • Place of Presentation
      Nagoya (poster)
    • Related Report
      2012 Final Research Report
  • [Presentation] コバルト触媒を用いた末端アルキンに対するメタノールの二重付加反応についての速度論的研究2011

    • Author(s)
      牛丸 理一郎,立浪 忠志,西村 拓歩,野依 良治,中 寛史
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば(ポスター)
    • Related Report
      2012 Final Research Report
  • [Presentation] Kinetic studies on the Double Addition of Methanol to Terminal Alkynes Catalyzed by Cobalt Complexes2011

    • Author(s)
      Richiro Ushimaru, Tadashi Tachinami, Takuho Nishimura, Ryoji Noyori, and Hiroshi Naka
    • Organizer
      第5回物質科学フロンティアセミナー
    • Place of Presentation
      名古屋
    • Related Report
      2012 Final Research Report 2011 Research-status Report
  • [Presentation] コバルト触媒を用いた末端アルキンの水和反応2011

    • Author(s)
      中 寛史
    • Organizer
      統合物質創製化学推進事業第二回若手研究会
    • Place of Presentation
      北海道千歳市
    • Related Report
      2012 Final Research Report
  • [Presentation] A Step Towards Robust Hydration of Organic Compounds Through Molecular Catalysis2011

    • Author(s)
      Hiroshi Naka
    • Organizer
      11thIRTG Joint Symposium
    • Place of Presentation
      Munster(invited lecture)
    • Related Report
      2012 Final Research Report
  • [Presentation] Kinetic studies on the Cobalt-Catalyzed Double Addition of Methanol to Terminal Alkynes2011

    • Author(s)
      R. Ushimaru, T. Tachinami, R. Noyori, and H. Naka
    • Organizer
      第4回グローバルCOE 化学 成果報告会
    • Place of Presentation
      名古屋
    • Related Report
      2011 Research-status Report
  • [Presentation] コバルト触媒を用いた末端アルキンに対するメタノールの二重付加反応についての速度論的研究2011

    • Author(s)
      牛丸理一郎・立浪忠志・西村拓歩・野依良治・中寛史
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば
    • Related Report
      2011 Research-status Report
  • [Presentation] Mechanistic Insights into the Cobalt-Catalyzed Double Addition of Methanol to Terminal Alkynes2011

    • Author(s)
      R. Ushimaru, T. Tachinami, T. Nishimura, R. Noyori, and H. Naka
    • Organizer
      12th IRTG Joint Symposium
    • Place of Presentation
      Nagoya
    • Related Report
      2011 Research-status Report
  • [Presentation] Mechanistic Insights into the Double Addition of Methanol to Terminal Alkynes Catalyzed by Cobalt complexes2011

    • Author(s)
      R. Ushimaru, T. Tachinami, T. Nishimura, R. Noyori, and H. Naka
    • Organizer
      7th and 8th Yoshimasa Hirata Memorial Lecture
    • Place of Presentation
      Nagoya
    • Related Report
      2011 Research-status Report
  • [Presentation] A Step Towards Robust Hydration of Organic Compounds Through Molecular Catalysis2011

    • Author(s)
      Hiroshi Naka
    • Organizer
      11th IRTG Joint Symposium(招待講演)
    • Place of Presentation
      Muenster, Germany
    • Related Report
      2011 Research-status Report
  • [Presentation] コバルト触媒を用いた末端アルキンの水和反応2011

    • Author(s)
      中 寛史
    • Organizer
      統合物質創製化学推進事業 第二回若手研究会
    • Place of Presentation
      北海道支笏湖
    • Related Report
      2011 Research-status Report
  • [Remarks] 名古屋大学理学部化学科HP, 紹介記事

    • URL

      http://www3.chem.nagoya-u.ac.jp/wordpress/?p=6642

    • Related Report
      2012 Final Research Report
  • [Remarks] 野依研究室HP, 紹介記事 (論文:ほぼ中性条件下でのアルキン水和反応)

    • Related Report
      2012 Final Research Report
  • [Remarks] 名古屋大学理学部化学科HP,紹介記事

    • URL

      http://www3.chem.nagoya-u.ac.jp/wordpress/?p=6642

    • Related Report
      2012 Annual Research Report
  • [Remarks] 野依研究室HP,紹介記事(論文:ほぼ中性条件下でのアルキン水和反応)

    • URL

      http://noy.chem.nagoya-u.ac.jp/noy_j/Top/entori/2012/12/19_lun_wenhobo_zhong_xing_tiao_jian_xiadenoarukin_shui_he_fan_ying.html

    • Related Report
      2012 Annual Research Report

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

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