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Palladium-Catalyzed Highly Selective Transformation of Allylic Substrates

Research Project

Project/Area Number 21750086
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

OHMIYA Hirohisa  北海道大学, 大学院・理学研究院, 准教授 (40508876)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsアリル化 / 位置選択性 / パラジウム触媒 / 銅触媒 / 有機ホウ素化合物 / 有機ケイ素化合物 / 立体特異性 / パラジウム / 銅 / 立体選択性 / C-H官能基化 / アリルアルコール基質 / クロスカップリング反応 / アリールホウ酸 / 不斉転写 / アニオン性配位子 / アリル系基質 / gem-ジアリールアルカン / (+)-sertraline
Research Abstract

Allylic alkylations with carbon nucleophiles are among the most important carbon. carbon bond formation methods in organic synthesis due to the versatility of the alkene functionality for stereoselective derivatization. Nevertheless, the reaction of unsymmetrically substituted secondary allylic substrates occurs competitively at theα-andγ-positions. To address the issue of the regiochemical control in the allylic substitution, palladium-or copper-catalyzed allylic alkylations of unsymmetrically substituted internal allylic alcohol substrates, which proceeded with excellentγ-selectivity and stereospecificity, have been developed.

Report

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

    (48 results)

All 2012 2011 2010 2009 Other

All Journal Article (24 results) (of which Peer Reviewed: 24 results) Presentation (23 results) Remarks (1 results)

  • [Journal Article] Regio- and Stereocontrolled Introduction of Secondary Alkyl Groups to Electron-Deficient Arenes through Copper-Catalyzed Allylic Alkylation2012

    • Author(s)
      槇田祐輔、大宮寛久、澤村正也
    • Journal Title

      Angewandte Chemie

      Volume: 51 Issue: 17 Pages: 4122-4127

    • DOI

      10.1002/anie.201200809

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Conjugated Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Aryl- or Alkenylboronates2012

    • Author(s)
      Mingyu Yang, Natsumi Yokokawa, Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 3 Pages: 816-819

    • DOI

      10.1021/ol2033465

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Preparation of β-Branched γ, δ-Unsaturated Esters through Copper-Catalyzed Allylic Alkylation of Ketene Silyl Acetal2012

    • Author(s)
      Dong Li, Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      Synthesis (PSP article)

      Volume: 44 Issue: 09 Pages: 1304-1307

    • DOI

      10.1055/s-0031-1289712

    • NAID

      120005228671

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] General Approach to Allenes through Copper-Catalyzed g-Selective and Stereospecific Coupling between Propargylic Phosphates and Alkylboranes2011

    • Author(s)
      大宮寛久、横堀海、槇田祐輔、澤村正也
    • Journal Title

      Organic Letters

      Volume: 13 Issue: 23 Pages: 6312-6315

    • DOI

      10.1021/ol202866h

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Conjugate Additions of Alkylboranes to Aryl α, β-Unsaturated Ketones2011

    • Author(s)
      Hirohisa Ohmiya, Yoshinori Shido, Mika Yoshida, Masaya Sawamura
    • Journal Title

      Chem. Lett.

      Volume: 40 Issue: 9 Pages: 928-930

    • DOI

      10.1246/cl.2011.928

    • NAID

      10029521633

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed γ-Selective and Stereospecific Allylic Alkylation of Ketene Silyl Acetals2011

    • Author(s)
      Dong Li, Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 133 Issue: 15 Pages: 5672-5675

    • DOI

      10.1021/ja111645q

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Carboxylation of Alkylboranes with Carbon Dioxide: Formal Reductive Carboxylation of Terminal Alkenes2011

    • Author(s)
      Hirohisa Ohmiya, Masahito Tanabe, Masaya Sawamura
    • Journal Title

      Org. Lett.

      Volume: 13 Issue: 5 Pages: 1086-1088

    • DOI

      10.1021/ol103128x

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Conjugate Additions of Alkylboranes to Imidazolyl α, β-Unsaturated Ketones ; Formal Reductive Conjugate Addition of TerminalAlkenes2011

    • Author(s)
      Hirohisa Ohmiya, Mika Yoshida, Masaya Sawamura
    • Journal Title

      Org. Lett.

      Volume: 13 Issue: 3 Pages: 482-485

    • DOI

      10.1021/ol102819k

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] General Approach to Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Alkylboranes2011

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 6312-6315

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Conjugated Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Aryl-or2011

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Org.Lett.

      Volume: 14 Pages: 816-819

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Conjugate Additions of Alkylboranes to Imidazolyl a,b-Unsaturated Ketones : Formal Reductive Conjugate Addition of Terminal Alkenes2011

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 482-485

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Carboxylation of Alkylboranes with Carbon Dioxide : Formal Reductive Carboxylation of Terminal Alkenes2011

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 1086-1088

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sulfonamidoquinoline-VPalladium(II) Dimer Complex As a Catalyst Precursor for Palladium-Catalyzed γ-Selective and Stereospecific Allyl-VAryl Coupling Reaction between Allylic Acetates and Arylboronic Acids2010

    • Author(s)
      Yusuke Makida, Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      Chem. Asian J.

      Volume: 6 Issue: 2 Pages: 410-414

    • DOI

      10.1002/asia.201000721

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of α-Arylated Allylsilanes through Palladium-Ctalyzed γ-Selective Allyl-Aryl Coupling2010

    • Author(s)
      Dong Li, Tatsunori Tanaka Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      Org. Lett.

      Volume: 12 Issue: 15 Pages: 3344-3347

    • DOI

      10.1021/ol101114r

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed γ-Selective and Stereospecific Allyl-Aryl Coupling between (Z)-Acyclic and Cyclic Allylic Phosphates and Arylboronates2010

    • Author(s)
      Hirohisa Ohmiya, Natsumi Yokokawa, Masaya Sawamura
    • Journal Title

      Org. Lett.

      Volume: 12 Issue: 10 Pages: 2438-2440

    • DOI

      10.1021/ol100841y

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed γ-Selective Allyl-VAlkyl Coupling between Allylic Phosphates and Alkylboranes2010

    • Author(s)
      Hirohisa Ohmiya, Umi Yokobori, Yusuke Makida, Masaya Sawamura
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 132 Issue: 9 Pages: 2895-2897

    • DOI

      10.1021/ja9109105

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed γ-Selective and Stereospecific Allyl-Aryl Coupling between Acyclic Allylic Esters and Arylboronic Acids2010

    • Author(s)
      Hirohisa Ohmiya, Yusuke Makida, Dong Li, Masahito Tanabe, Masaya Sawamura
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 132 Issue: 2 Pages: 879-889

    • DOI

      10.1021/ja9092264

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed γ-Selective and Stereospecific Allyl-Aryl Coupling between (Z)-Acyclic and Cyclic Allylic Phosphates and Arylboronates2010

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 2438-2440

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a-Arylated Allylsilanes through Palladium-Ctalyzed g-Selective Allyl-Aryl Coupling2010

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 3344-3347

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sulfonamidoquinoline-Palladium(II) Dimer Complex As a Catalyst Precursor for Palladium-Catalyzed g-Selective and Stereospecific Allyl-Aryl Coupling Reaction between Allylic Acetates and Arylboronic Acids2010

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Chem.Asian J.

      Volume: 6 Pages: 410-414

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed γ-Selective and Stereospecific Allyl-Aryl Coupling between Acyclic Allylic Esters and Arylboronic Acids2010

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 879-889

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed γ-Selective Allyl-Alkyl Coupling between Allylic Phosphates and Alkylboranes2010

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 2895-2897

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] General and Functional Group-Tolerable Approach to Allenylsilanes by Rhodium-Catalyzed Coupling between Propargylic Carbonates and a Silylboronate2009

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Org.Lett. 11

      Pages: 5618-5620

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cu(I)-Catalyzed Intramolecular Hydroamination of Unactivated Alkenes Bearing a Primary or Secondary Amino Group in Alcoholic Solvents2009

    • Author(s)
      Hirohisa Ohmiya
    • Journal Title

      Org.Lett. 11

      Pages: 2145-2147

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 位置および立体制御された遷移金属触媒アリル化反応の開発2012

    • Author(s)
      大宮寛久
    • Organizer
      平成23年度日本化学会北海道支部奨励賞受賞講演会
    • Place of Presentation
      北海道大学,札幌市
    • Year and Date
      2012-02-01
    • Related Report
      2011 Final Research Report
  • [Presentation] 有機ホウ素化合物を用いる高選択的炭素-炭素結合形成反応の開発2012

    • Author(s)
      大宮寛久
    • Organizer
      若い世代の特別講演会
    • Place of Presentation
      慶應義塾大学,横浜市
    • Related Report
      2011 Final Research Report
  • [Presentation] 有機ホウ素化合物を用いる高選択的炭素-炭素結合形成反応の開発2012

    • Author(s)
      大宮寛久
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学(横浜市)
    • Related Report
      2011 Annual Research Report
  • [Presentation] アリル化の反応位置を究める2011

    • Author(s)
      大宮寛久
    • Organizer
      京都薬科大学薬化学分野学術講演会
    • Place of Presentation
      京都市
    • Year and Date
      2011-09-20
    • Related Report
      2011 Final Research Report
  • [Presentation] アリル化の反応位置を究める2011

    • Author(s)
      大宮寛久
    • Organizer
      京都薬科大学薬化学分野学術講演会
    • Place of Presentation
      京都薬科大学(京都市)(招待講演)
    • Year and Date
      2011-09-20
    • Related Report
      2011 Annual Research Report
  • [Presentation] アリル化の反応位置を究める2011

    • Author(s)
      大宮寛久
    • Organizer
      京都大学大学院理学研究科講演会
    • Place of Presentation
      京都市
    • Year and Date
      2011-09-17
    • Related Report
      2011 Final Research Report
  • [Presentation] アリル化の反応位置を究める2011

    • Author(s)
      大宮寛久
    • Organizer
      京都大学大学院理学研究科講演会
    • Place of Presentation
      京都大学(京都市)(招待講演)
    • Year and Date
      2011-09-17
    • Related Report
      2011 Annual Research Report
  • [Presentation] 有機ホウ素化合物を用いる高選択的炭素-炭素結合形成反応の開発2011

    • Author(s)
      大宮寛久
    • Organizer
      日本化学会第91春季年会 「若い世代の特別講演会」
    • Place of Presentation
      神奈川県横浜市
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] Regio-and Stereocontrolled Transition Metal Catalysis on Allylic Systems2011

    • Author(s)
      Hirohisa Ohmiya
    • Organizer
      ISOMC 2011
    • Place of Presentation
      Osaka University, Osaka
    • Related Report
      2011 Final Research Report
  • [Presentation] 銅触媒によるケテンシリルアセタール類のγ位選択的立体特異的アリル位アルキル化反応2011

    • Author(s)
      大宮寛久、李棟、澤村正也
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学,名古屋市
    • Related Report
      2011 Final Research Report
  • [Presentation] Copper-Catalyzed Carbon-Carbon Bond Formation Reactions with Alkylboranes2011

    • Author(s)
      Hirohisa Ohmiya, Umi Yokobori, Mika Yoshida, Kazunori Nagao, Masahito Tanabe, Yusuke Makida, Masaya Sawamura
    • Organizer
      OMCOS 16
    • Place of Presentation
      Shanghai
    • Related Report
      2011 Final Research Report
  • [Presentation] 有機ホウ素化合物を用いる高選択的炭素-炭素結合形成反応の開発2011

    • Author(s)
      大宮寛久
    • Organizer
      統合物質第2回若手研究会
    • Place of Presentation
      休暇村支笏湖,千歳市
    • Related Report
      2011 Final Research Report
  • [Presentation] Copper-Catalyzea Carbon-Carbon Bond Formation Reactions with Alkylboranes2011

    • Author(s)
      Hirohisa Ohmiya
    • Organizer
      OMCOS16
    • Place of Presentation
      Shanghai International Convention Center(中国)
    • Related Report
      2011 Annual Research Report
  • [Presentation] 銅触媒によるケテンシリルアセタール類のγ位選択的立体特異的アリル位アルキル化反応2011

    • Author(s)
      大宮寛久
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学(名古屋市)
    • Related Report
      2011 Annual Research Report
  • [Presentation] Regio- and Stereocontrolled Transition Metal Catalysis on Allylic Systems2011

    • Author(s)
      Hirohisa Ohmiya
    • Organizer
      ISOMC2011
    • Place of Presentation
      大阪大学(豊中市)(招待講演)
    • Related Report
      2011 Annual Research Report
  • [Presentation] アリル型化合物の位置選択的クロスカップリング反応2010

    • Author(s)
      大宮寛久
    • Organizer
      若手研究者のための有機化学札幌セミナー
    • Place of Presentation
      北海道大学,札幌市
    • Year and Date
      2010-02-02
    • Related Report
      2011 Final Research Report
  • [Presentation] アリル型化合物の位置選択的クロスカップリング反応2010

    • Author(s)
      大宮寛久
    • Organizer
      若手研究者のための有機化学札幌セミナー
    • Place of Presentation
      北海道大学 工学部
    • Year and Date
      2010-02-02
    • Related Report
      2009 Annual Research Report
  • [Presentation] 銅触媒によるアリルおよびプロパルギルアルコール誘導体とアルキルホウ素化合物のγ選択的カップリング反応2010

    • Author(s)
      大宮寛久、横堀海、槇田祐輔、澤村正也
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学,八王子市
    • Related Report
      2011 Final Research Report
  • [Presentation] 銅触媒によるアリルおよびプロパルギルアルコール誘導体とアルキルホウ素化合物のγ選択的カップリング反応2010

    • Author(s)
      大宮寛久
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      東京都八王子市
    • Related Report
      2010 Annual Research Report
  • [Presentation] パラジウム触媒による(C)選択的および立体特異的アリル-アリールカップリング反応2009

    • Author(s)
      大宮寛久、槇田祐輔、李棟、田辺正人、澤村正也
    • Organizer
      第96回有機合成シンポジウム
    • Place of Presentation
      早稲田大学,東京都新宿区
    • Related Report
      2011 Final Research Report
  • [Presentation] パラジウム触媒によるアリルエステル類とアリールホウ酸のγ位選択的および立体特異的アリル-アリールカップリング反応2009

    • Author(s)
      大宮寛久、槇田祐輔、田辺正人、李棟、澤村正也
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学,京都市
    • Related Report
      2011 Final Research Report
  • [Presentation] パラジウム触媒による(c)選択的および立体特異的アリル-アリールカップリング反応2009

    • Author(s)
      大宮寛久
    • Organizer
      第96回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Related Report
      2009 Annual Research Report
  • [Presentation] Palladium-Catalyzed γ-Selective and Stereospecific Allyl-Aryl Coupling between Allylic Esters and Arylboronic Acids2009

    • Author(s)
      大宮寛久
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学今出川キャンパス
    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://wwwchem.sci.hokudai.ac.jp/~orgmet/

    • Related Report
      2011 Final Research Report

URL: 

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

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