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Investigation of Active Palladium Catalyst Based on Novel Ruthenocenylphosphine Ligand and its Application to Cross-Coupling Reaction

Research Project

Project/Area Number 21550100
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionNiigata University

Principal Investigator

HOSHI Takashi  新潟大学, 自然科学系, 助教 (20303175)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2010: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2009: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywordsクロスカップリング / パラジム触媒 / ホスフィン配位子 / パラジウム触媒 / ホスフィン / 配位子 / 鈴木-宮浦 / C-H結合活性化 / ビアリール / ヘテロビアリール / 鈴木-宮浦反応
Research Abstract

A highly general, active, and stable catalytic system was realized in the palladium-catalyzed Suzuki-Miyaura reactions of sterically and/or electronically deactivated aryl chlorides and aminochloropyridines with arylboronic acids using a palladium precatalyst prepared from di-cyclo-hexylruthenocenylphosphine(CyR-Phos), Pd(dba)_2, and ethyl 4-bromobenzoate. The relatively weak basicity and highly steric hindrance of R-Phos, di-tert-butyl analogue of CyR-Phos, was disclosed on the basis of the JP-Se coupling constant and the crystal structure of the phosphine selenide derivative. These results suggest that not the electron donation but the steric bulkiness is the key element of the ligand architecture of R-Phos family to activate the palladium catalyst.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (31 results)

All 2012 2011 2010 2009

All Journal Article (6 results) (of which Peer Reviewed: 3 results) Presentation (25 results)

  • [Journal Article] Highly Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles Using Sulfur-MOP Ligand2011

    • Author(s)
      Hoshi, Takashi ; Sasaki, Koji ; Sato, Shun ; Ishii, Yuichi ; Suzuki, Toshio ; Hagiwara, Hisahiro
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 932-935

    • Related Report
      2011 Final Research Report
  • [Journal Article] A Highly Sustainable and Active Catalyst for Suzuki-Miyaura Reaction : Palladium-Supported Ionic Liquid Catalyst(SILC) Coated with Polymer2011

    • Author(s)
      Hagiwara, H.; Sato, K.; Hoshi, T.; Suzuki, T
    • Journal Title

      SYNLETT

      Pages: 2545-2550

    • Related Report
      2011 Final Research Report
  • [Journal Article] A Highly Sustainable and Active Catalyst for Suzuki-Miyaura Reaction : Palladium-Supported Ionic Liquid Catalyst (SILC) Coated with Polymer2011

    • Author(s)
      Hagiwara, H.; Sato, K.; Hoshi, T.; Suzuki, T.
    • Journal Title

      SYNLETT

      Volume: 2011 Issue: 17 Pages: 2545-2550

    • DOI

      10.1055/s-0030-1260322

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles Using Sulfur-MOP Ligand2011

    • Author(s)
      星隆
    • Journal Title

      Organic Letters

      Volume: 13 Pages: 942-935

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Biphenylene-Substituted Ruthenocenylphosphine for Suzuki. Miyaura Coupling of Sterically Hindered Aryl Bromides2009

    • Author(s)
      Hoshi, Takashi ; Saitoh, Ippei ; Nakazawa, Taichi ; Suzuki, Toshio ; Sakai, Jun-ichi ; Hagiwara, Hisahiro
    • Journal Title

      J. Org. Chem

      Volume: 74 Pages: 4013-4016

    • Related Report
      2011 Final Research Report
  • [Journal Article] Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Sterically Hindered Aryl Bromides2009

    • Author(s)
      星隆
    • Journal Title

      The Journal of Organic Chemistry 74

      Pages: 4013-4016

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 鈴木-宮浦反応におけるビフェニレン置換ルテノセニルホスフィン配位子(R-Phos)のパラジウム触媒活性化機能2012

    • Author(s)
      星隆
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学(神奈川)
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] 鈴木-宮浦反応におけるビフェニレン置換ルテノセニルホスフィン配位子(R-Phos)のパラジウム触媒活性化機能(Activation of Palladium Catalyst by Biphenylene-Substituted Ruthenocenylphosphine(R-Phos) in Suzuki-Miyaura Reaction)2012

    • Author(s)
      星隆・佐藤努・萩原久大・鈴木敏夫
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Related Report
      2011 Final Research Report
  • [Presentation] クロスカップリング反応に関する基礎から最先端研究の動向まで2011

    • Author(s)
      星隆
    • Organizer
      第4回新潟大学・信越化学技術交流会
    • Place of Presentation
      信越化学工業株式会社・シリコーン電子材料技術研究所
    • Year and Date
      2011-12-02
    • Related Report
      2011 Final Research Report
  • [Presentation] 高度パラジウム触媒活性化配位子R-Phosの機能解明を目的とするかさ高い基質を用いた鈴木-宮浦反応2011

    • Author(s)
      星隆
    • Organizer
      第62回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟大学(新潟)
    • Year and Date
      2011-11-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] 光学活性P,S-二座配位子Sulfur-MOPを用いるインドールの高エナンチオ選択的パラジウム触媒アリル化反応2011

    • Author(s)
      星隆
    • Organizer
      日本化学会第5回関東支部大会
    • Place of Presentation
      東京農工大(東京)
    • Year and Date
      2011-08-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] ビフェニレン置換ジシクロヘキシルルテノセニルポスフィン(CyR-Phos)の配位により高度に活性化されたパラジウム触媒を用いる鈴木-宮浦反応2011

    • Author(s)
      星隆
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] 鈴木-宮浦反応に用いる高活性パラジウム触媒の開発研究から見たクロスカップリング反応の過去、現在、未来2011

    • Author(s)
      星隆
    • Organizer
      第126回講演会.技術・学術講演.「限界に挑戦する有機合成化学.基礎からプロセスまで」
    • Place of Presentation
      新潟大学
    • Year and Date
      2011-02-23
    • Related Report
      2011 Final Research Report
  • [Presentation] 高度パラジウム触媒活性化配位子R-Phosの機能解明を目的とするかさ高い基質を用いた鈴木-宮浦反応2011

    • Author(s)
      星隆・佐藤努・萩原久大・鈴木敏夫
    • Organizer
      第62回有機合成化学協会関東支部シンポジウム(新潟シンポジウム)
    • Place of Presentation
      新潟大学
    • Related Report
      2011 Final Research Report
  • [Presentation] 光学活性P, S-二座配位子Sulfur-MOPを用いるインドールの高エナンチオ選択的パラジウム触媒アリル化反応2011

    • Author(s)
      星隆・石井悠一・佐々木幸司・鈴木敏夫・萩原久大
    • Organizer
      日本化学会第5回関東支部大会
    • Place of Presentation
      東京農工大学
    • Related Report
      2011 Final Research Report
  • [Presentation] ビフェニレン置換ジシクロヘキシルルテノセニルホスフィン(CyR-Phos)の配位により高度に活性化されたパラジウム触媒を用いる鈴木-宮浦反応(Highly Active Palladium Catalyst for Suzuki-Miyaura Reaction Bearing Biphenylene-Substituted Dicyclohexylruthenocenylphosphine(CyR-Phos))2011

    • Author(s)
      星隆・本間知之・鈴木敏夫・萩原久大
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学
    • Related Report
      2011 Final Research Report
  • [Presentation] 新規ルテノセニルホスフィン配位子(CyR-Phos)によるパラジウム触媒の活性化と低反応性基質を用いる鈴木-宮浦反応への応用2010

    • Author(s)
      星隆・本間知之・鈴木敏夫・萩原久大
    • Organizer
      第60回有機合成化学協会関東支部シンポジウム(新潟シンポジウム)
    • Place of Presentation
      新潟薬科大学
    • Year and Date
      2010-12-04
    • Related Report
      2011 Final Research Report
  • [Presentation] Highly Enantioselective Allylic Alkylatin of Indoles Catalyzed by Palladium Complex with Chiral Sulfur-MOP Ligand2010

    • Author(s)
      星隆
    • Organizer
      第57回有機金属討論会
    • Place of Presentation
      中央大学(東京)
    • Year and Date
      2010-09-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] 新規ビフェニレン置換ルテノセニルホスフィン配位子を用いる高活性長寿命パラジウム触媒の開発と鈴木-宮浦反応への応用2010

    • Author(s)
      星隆・齋藤一平・中澤太一・鈴木敏夫・萩原久大
    • Organizer
      第59回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京農工大学
    • Year and Date
      2010-05-22
    • Related Report
      2011 Final Research Report
  • [Presentation] 新規ビフェニレン置換ルテノセニルポスフィン配位子を用いる高活性長寿命パラジウム触媒の開発と鈴木-宮浦反応への応用2010

    • Author(s)
      星隆
    • Organizer
      第59回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京農工大(東京)
    • Year and Date
      2010-05-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] 新規ルテノセニルホスフィン配位子(CyR-Phos)から調製される長期保存可能な高活性2価パラジウム触媒前駆体の開発と鈴木-宮浦反応への応用2010

    • Author(s)
      星隆
    • Organizer
      第90回日本化学会春季年会
    • Place of Presentation
      近畿大学(大阪)
    • Year and Date
      2010-03-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] 光学活性P, S-二座配位子Sulfur-MOPを用いるインドールの高エナンチオ選択的パラジウム触媒アリル化反応(Highly Enantioselective Allylic Alkylation of Indoles Catalyzed by Palladium Complex with Chiral Sulfur-MOP Ligand)2010

    • Author(s)
      星隆・佐々木幸司・石井悠一・鈴木敏夫・萩原久大
    • Organizer
      第57回有機金属化学討論
    • Place of Presentation
      中央大学
    • Related Report
      2011 Final Research Report
  • [Presentation] 新規ルテノセニルホスフィン配位子(CyR-Phos)から調製される長期保存可能な高活性2価パラジウム触媒前駆体の開発と鈴木-宮浦反応への応用(Active and Storable Palladium(II) Precatalyst Based on Di-cyclo-hexylruthenocenylphosphine(CyR-Phos) and its Application to Suzuki-Miyaura Reaction)2010

    • Author(s)
      星隆・本間知之・森彩子・鈴木敏夫・萩原久大
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Related Report
      2011 Final Research Report
  • [Presentation] Active and Stable Palladium Catalyst Based on Biphenylene-Substituted Ruthenocenylphine (R-Phos) for Suzuki-Miyaura Reaction of Sterically Hindered Aryl Halides2009

    • Author(s)
      星隆
    • Organizer
      The Eleventh International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-11)
    • Place of Presentation
      リーガ・ロイヤルホテル京都(京都)
    • Year and Date
      2009-11-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] Active and Stable Palladium Catalyst Based on Biphenylene-Substituted Ruthenocenylphosphine Ligand (R-Phos) and its Application to Suzuki-Miyaura Reaction of Sterically Hindered Aryl Halides2009

    • Author(s)
      星隆
    • Organizer
      第56回有機金属討論会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2009-09-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Sterically Hindered Aryl Bromides2009

    • Author(s)
      星隆
    • Organizer
      15^<th> IUPAC International Symposium on organometallic Chemistry Directed Toward Organic Synthesis (OMCOS 15)
    • Place of Presentation
      Glasgow Royal Concert Hall (Glasgow, UK)
    • Year and Date
      2009-07-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 光学活性P, S-配位子Sulfur-MOPを用いるインドールのパラジウム触媒不斉アリル化反応2009

    • Author(s)
      星隆・佐々木幸司・鈴木敏夫・萩原久大
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム(新潟シンポジウム)
    • Place of Presentation
      長岡技術科学大学
    • Related Report
      2011 Final Research Report
  • [Presentation] 新規ビフェニレン置換ルテノセニルホスフィン配位子(R-Phos)から調整される高活性長寿命パラジウム触媒の応用研究:かさ高い基質を用いる鈴木-宮浦反応2009

    • Author(s)
      星隆・齋藤一平・中澤太一・鈴木敏夫・萩原久大
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム(新潟シンポジウム)
    • Place of Presentation
      長岡技術科学大学
    • Related Report
      2011 Final Research Report
  • [Presentation] Active and Stable Palladium Catalyst Based on Biphenylene-Substituted Ruthenocenylphosphine(R-Phos) for Suzuki-Miyaura Reaction of Sterically Hindered Aryl Halides2009

    • Author(s)
      Takashi Hoshi, Ippei Saitoh, Taichi Nakazawa, Tomonobu Honnma, Toshio Suzuki, Hisahiro Hagiwara
    • Organizer
      The Tenth International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-11)
    • Place of Presentation
      Kyoto
    • Related Report
      2011 Final Research Report
  • [Presentation] ビフェニレン置換ルテノセニルホスフィン配位子(R-Phos)から調整される高活性長寿命パラジウム触媒の応用研究:かさ高い芳香族ハロゲン化物を用いる鈴木-宮浦反応(Active and Stable Palladium Catalyst Based on Biphenylene-Substituted Ruthenocenylphosphine Ligand(R-Phos) and its Application to Suzuki-Miyaura Reaction of Sterically Hinder2009

    • Author(s)
      星隆・齋藤一平・本間知之・中澤太一・鈴木敏夫・萩原久大
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学
    • Related Report
      2011 Final Research Report
  • [Presentation] Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Sterically Hindered Aryl Bromides2009

    • Author(s)
      Takashi Hoshi, Ippei Saitoh, Taichi Nakazawa, Toshio Suzuki, Hisahiro Hagiwara
    • Organizer
      15th IUPAC International Symposium on organometallic Chemistry Directed Toward Organic Synthesis(OMCOS 15)
    • Place of Presentation
      Glasgow
    • Related Report
      2011 Final Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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