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2012 Fiscal Year Final Research Report

Hydration of organic compounds catalyzed by metal porphyrins

Research Project

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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
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
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.

  • Research Products

    (17 results)

All 2013 2012 2011 Other

All Journal Article (1 results) Presentation (14 results) Remarks (2 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

  • [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)
    • Year and Date
      20130322-25
  • [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)
    • Year and Date
      20130322-25
  • [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)
    • Year and Date
      20121210-11
  • [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)
    • Year and Date
      20120915-20
  • [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).
    • Year and Date
      20120915-20
  • [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)
    • Year and Date
      20120601-02
  • [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
    • Year and Date
      20120325-28
  • [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)
    • Year and Date
      20111128-30
  • [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
    • Year and Date
      20111021-22
  • [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)
    • Year and Date
      20111003-04
  • [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)
    • Year and Date
      20110921-23
  • [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
    • Year and Date
      20110527-28
  • [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)
    • Year and Date
      20110509-10
  • [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
  • [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

  • [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

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Published: 2014-09-25  

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