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Development of Organic Transforming Reaction with a Trace Amount of Highly Active NNC-Pincer Complexes

Research Project

Project/Area Number 17K14524
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Green/Environmental chemistry
Research InstitutionInstitute for Molecular Science

Principal Investigator

Hamasaka Go  分子科学研究所, 生命・錯体分子科学研究領域, 助教 (50570230)

Research Collaborator Uozumi Yasuhiro  
Ichii Shun  
Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsパラジウム / ピンサー型錯体 / 溝呂木ーヘック反応 / 檜山反応 / ppm / ピンサー錯体 / 痕跡量触媒 / クロスカップリング反応
Outline of Final Research Achievements

We examined to develop the carbon-carbon bond forming reaction catalyzed by a ppm loading amount of a catalyst. A ppb to ppm loading amount of a palladium NNC-pincer complex catalyzed the Mizorki-Heck reaction of aryl halides with activated terminal alkenes and the Hiyama reaction of aryl bromides with aryltrialcoxysilanes to give the corresponding products in good yields. Various functional groups were tolerated in this catalytic system. In particular, low reactive heteroaromatic halides also underwent the reaction efficiently to give the corresponding products. In our catalytic system, turn over number and turn over frequency reached 870,000,000 and 3360 per second, respectively.

Academic Significance and Societal Importance of the Research Achievements

現在、我々の豊かな生活を実現する上で有機合成化学は重要な役割を果たしてきた。特に、触媒的有機分子変換は、一般に困難な分子変換工程を実現するなど、医薬品や機能性材料の合成において欠くことのできない手法である。このような触媒的有機分子変換では、パラジウムに代表される希少遷移金属が触媒として用いられている。しかしながら、遷移金属の地殻埋蔵量が少ないための将来的な枯渇と、遷移金属の生成物中への混入が問題とされてきた。本研究で得られた、ppmオーダー以下で機能する触媒システムは、これらの問題を解決するための一つの方法を提供するものであり、社会的にも学術的にも高い意義があると考えられる。

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (20 results)

All 2019 2018 2017 Other

All Int'l Joint Research (1 results) Journal Article (7 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 7 results,  Open Access: 2 results) Presentation (10 results) (of which Int'l Joint Research: 4 results,  Invited: 1 results) Patent(Industrial Property Rights) (2 results) (of which Overseas: 1 results)

  • [Int'l Joint Research] Colby College(米国)

    • Related Report
      2017 Research-status Report
  • [Journal Article] Mechanistic insight into the catalytic hydrogenation of nonactivated aldehydes with a Hantzsch ester in the presence of a series of organoboranes: NMR and DFT studies2019

    • Author(s)
      Go Hamasaka, Hiroaki Tsuji, Masahiro Ehara, Yasuhiro Uozumi
    • Journal Title

      RSC Adv.

      Volume: 9 Issue: 18 Pages: 10201-10210

    • DOI

      10.1039/c9ra01468c

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Palladium NNC-Pincer Complex as an Efficient Catalyst Precursor for the Mizoroki-Heck Reaction2018

    • Author(s)
      Hamasaka Go、Ichii Shun、Uozumi Yasuhiro
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 360 Issue: 9 Pages: 1833-1840

    • DOI

      10.1002/adsc.201800099

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Linear polystyrene-stabilized Rh(III) nanoparticles for oxidative coupling of arylboronic acids with alkenes in water2018

    • Author(s)
      Atsushi Ohtaka, Shiho Fukui, Akira Sakon, Go Hamasaka, Yasuhiro Uozumi, Tsutomu Shinagawa, Osamu Shimomura, Ryoki Nomura
    • Journal Title

      J. Organomet. Chem.

      Volume: 873 Pages: 1-7

    • DOI

      10.1016/j.jorganchem.2018.07.037

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Poly(tetrafluoroethylene)-Stabilized Metal Nanoparticles: Preparation and Evaluation of Catalytic Activity for Suzuki, Heck, and Arene Hydrogenation in Water2018

    • Author(s)
      Ohtaka Atsushi、Kawase Misa、Aihara Shunichiro、Miyamoto Yasuhiro、Terada Ayaka、Nakamura Kenta、Hamasaka Go、Uozumi Yasuhiro、Shinagawa Tsutomu、Shimomura Osamu、Nomura Ryoki
    • Journal Title

      ACS Omega

      Volume: 3 Issue: 8 Pages: 10066-10073

    • DOI

      10.1021/acsomega.8b01338

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Asymmetric Copper-Catalyzed C(sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones2018

    • Author(s)
      Takao Osako, Makoto Nagaosa, Go Hamasaka, Yasuhiro Uozumi
    • Journal Title

      Synlett

      Volume: 29 Pages: 2251-2256

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic specificity of linear polystyrene-stabilized Pd nanoparticles during Ullmann coupling reaction in water and the associated mechanism2018

    • Author(s)
      Atsushi Ohtaka, Akira Sakon, Asuka Yasui, Taira Kawaguchi, Go Hamasaka, Yasuhiro Uozumi, Tsutomu Shinagawa, Osamu Shimomura, Ryoki Nomura
    • Journal Title

      J. Organomet. Chem.

      Volume: 854

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Poly(meta-phenylene oxides) for the design of a tunable, efficient, and reusable catalytic platform2018

    • Author(s)
      Reuben H Hudson, Haoran Zhang, Amy LoTemplio, Georganna Benedetto, Go Hamasaka, Yoichi M. A. Yamada, Jeffrey Louis Katz, Yasuhiro Uozumi
    • Journal Title

      Chem. Commun.

      Volume: 54 Issue: 23 Pages: 2878-2881

    • DOI

      10.1039/c8cc00774h

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Development of the Highly Efficient Hiyama Coupling Reaction Using Ppm Loading Amount of a Palladium-NNC Pincer Complex2019

    • Author(s)
      Shun Ichii, Go Hamasaka, Yasuhiro Uozumi
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 有機ホウ素化合物を触媒としたアルデヒドのハンチエステルによる水素化反応の反応機構研究2019

    • Author(s)
      浜坂 剛, 辻 裕章, 江原正博, 魚住泰広
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ppm 量のパラジウム -NNC ピンサー型錯体による高効率檜山カップリング反応の開発2018

    • Author(s)
      市位 駿, 浜坂 剛, 魚住泰広
    • Organizer
      日本プロセス化学会2018サマーシンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] Self-Assembling Vesicle Formation and Its Catalytic Applications in Water of an Amphiphilic Palladium NCN-Pincer Complex2018

    • Author(s)
      Go Hamasaka, Tsubasa Muto, Yoshimichi Andoh, Kazushi Fujimoto, Kenichi Kato, Masaki Takata, Susumu Okazaki, Yasuhiro Uozumi
    • Organizer
      43rd International Conference on Coordination Chemistry (ICCC2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] パラジウム -NNC ピンサー型錯体による高効率檜山カップリング反応の開発2018

    • Author(s)
      浜坂 剛, 市位 駿, 魚住泰広
    • Organizer
      第44回反応と合成の進歩シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] Development of New Reaction Systems Driven by Assembly of Molecular Transition Metal Catalysts2018

    • Author(s)
      Go Hamasaka
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] ベシクル状自己組織化両親媒性ピンサー型錯体の形成・構造解析・触媒機能2017

    • Author(s)
      浜坂 剛, 武藤 翼, 安藤嘉倫, 藤本和士, 加藤健一, 高田昌樹, 岡崎 進, 魚住泰広
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] A Vesicular Self-Assembled Platinum NCN-Pincer Complex Catalyzed Hydrosilylation of Alkenes in Water2017

    • Author(s)
      Go Hamasaka, Yasuhiro Uozumi
    • Organizer
      The 19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS19)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] A Palladium NNC-Pincer Complex as an Extremely Efficient Catalyst Precursor for the Mizoroki-Heck Reaction2017

    • Author(s)
      Shun Ichii, Go Hamasaka, Yasuhiro Uozumi
    • Organizer
      The 19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS19)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] The Suzuki-Miyaura Cross-Coupling with a Palladium Catalyst at Parts Per Million Levels2017

    • Author(s)
      David Roy, Go Hamasaka, Yasuhiro Uozumi
    • Organizer
      The 19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS19)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Patent(Industrial Property Rights)] 脱離基を有する有機化合物と有機ケイ素化合物とのカップリング体の製造方法2019

    • Inventor(s)
      魚住泰広、浜坂剛、市位駿
    • Industrial Property Rights Holder
      自然科学研究機構
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2018 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 脱離基を有する有機化合物と有機ケイ素化合物とのカップリング体の製造方法2018

    • Inventor(s)
      魚住泰広、浜坂剛、市位駿
    • Industrial Property Rights Holder
      大学共同利用機関法人 自然科学研究機構
    • Industrial Property Rights Type
      特許
    • Filing Date
      2018
    • Related Report
      2017 Research-status Report

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Published: 2017-04-28   Modified: 2022-02-21  

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