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Development of Gold-and Palladium-catalyzed New Transformations via Modification of Ligands

Research Project

Project/Area Number 20350015
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTohoku University

Principal Investigator

YAMAMOTO Yoshinori  東北大学, 原子分子材料科学高等研究機構, 教授 (60029519)

Co-Investigator(Kenkyū-buntansha) JIN Tienan  東北大学, 原子分子材料科学高等研究機構, 准教授 (80431493)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥19,240,000 (Direct Cost: ¥14,800,000、Indirect Cost: ¥4,440,000)
Fiscal Year 2010: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2009: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2008: ¥7,150,000 (Direct Cost: ¥5,500,000、Indirect Cost: ¥1,650,000)
Keywords反応有機化学 / 金触媒 / パラジウム触媒 / リン配位子効果 / ヒドロチオル化 / 三成分環化反応 / 連続的環化反応 / D-A-D有機光電材料 / 炭素-炭素多結合活性化 / カチオン性金触媒 / アレン化合物 / アルキン化合物 / よう素反応剤 / 複素環 / 不斉ヒドロアミノ化 / アルキン / アレン / 不斉配位子
Research Abstract

Novel Pd-and Au-catalyzed molecular transformations have been developed through the modification of ligands and counter anions which showed high reactivity and selectivity. A variety of Norbornane derivatives have been synthesized and successfully used in the Pd-catalyzed asymmetric intramolecular hydroamination of alkynes. The newly prepared (R, R)-methyl norphos and (R, R)-toly renorphos afforded N-containing heterocyles in high yields and high enantio-selectivity. Moreover, novel Pd-catalyzed allylative dearomatization and three-component cycloaddition were developed. We have succeeded in development of cationic Au-catalyzed hydroalkoxylation and hydrothiolation. Moreover, we also succeeded in construction of thienocarbazole frameworks via a new Au-catalyzed cascade cyclization of arydiynes, which was further applied in the synthesis of D-A-D organic electronic materials. Various O-, S-and N-containing heterocyles bearing diiodine substituents have been synthesized through the facile and efficient electrophilic iodocyclizations.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (43 results)

All 2012 2011 2010 2009 2008 Other

All Journal Article (24 results) (of which Peer Reviewed: 24 results) Presentation (13 results) Book (3 results) Remarks (3 results)

  • [Journal Article] Synthesis of new donor-acceptor-donor materials via Au-catalyzed double cascade cyclization2012

    • Author(s)
      Ferrara Giovanni, Jin Tienan, Oniwa Kazuaki, Zhao Jian, Asiri Abdullah M., Yamamoto Yoshinori
    • Journal Title

      Tetrahedron Lett

      Volume: 53 Pages: 914-918

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed bisfunctionalization of active alkenes by .-acetonitrile-allyl addition : application to the synthesis of unsymmetric 1, 4-di(organo)fullerene derivatives2012

    • Author(s)
      Lu Shirong, Jin Tienan, Bao Ming, Asiri Abdullah M., Yamamoto Yoshinori
    • Journal Title

      Tetrahedron Lett

      Volume: 53 Pages: 1210-1213

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of new donor-acceptor-donor materials via Au-catalyzed double cascade cyclization2012

    • Author(s)
      Giovanni Ferrara, Tienan Jin, Kazuaki Oniwa, Jian Zhao, Abdullah M.Asiri, Yoshinori Yamamoto
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Pages: 914-918

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed bisfunctionalization of active alkenes by β-acetonitrile-α-allyl addition : application to the synthesis of unsymmetric 1,4-di(organo)fullerene derivatives2012

    • Author(s)
      Shirong Lu, Tienan Jin, Ming Bao, Abdullah M.Asiri, Yoshinori Yamamoto
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Pages: 1210-1213

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of 3, 4-dihalofurans via electrophilic iodocyclization2011

    • Author(s)
      Yang Fan, Jin Tienan, Bao Ming, Yamamoto, Yoshinori
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 4541-4543

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of diiodinated dihydronaphthalenes and naphthalenes via iodine mediated electrophilic cyclization2011

    • Author(s)
      Yang Fan, Jin Tienan, Bao Ming, Yamamoto, Yoshinori
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 4013-4015

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of 3, 4-diiododihydrothiophenes via electrophilic iodocyclization2011

    • Author(s)
      Yang Fan, Jin Tienan, Bao Ming, Yamamoto, Yoshinori
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Pages: 936-938

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Three-Component [3+ 2] Cycloaddition of Propargyl Trifluoroacetates, Ethylidene Malonitriles, and Allyltributylstannane2010

    • Author(s)
      Lu Shirong, Jin Tienan, Bao Ming, Yamamoto Yoshonori
    • Journal Title

      Org. Lett.

      Volume: 12 Pages: 864-866

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene2010

    • Author(s)
      Huo Zhibao, Gridnev Ilya D, Yamamoto Yoshinori
    • Journal Title

      J. Org. Chem

      Volume: 75 Pages: 1266-1270

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Gold-catalyzed regiospecific intermolecular hydrothiolation of allenes2010

    • Author(s)
      Menggenbateer, Narsireddy Meda, Ferrara Giovanni, Nishina Naoko, Jin Tienan, Yamamoto Yoshinori
    • Journal Title

      Tetrahedron Lett

      Volume: 51 Pages: 4627-4629

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Gold-catalyzed regiospecific intermolecular hydrothiolation of allenes2010

    • Author(s)
      Menggenbateer, Medal Narsireddy, Giovanni Ferrara, Naoko Nishina, Tienan Jin, Yoshinori Yamamoto
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 4627-4629

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Three-Coinponent [3+2] Cycloaddition of Propargyl Trifluoroacetates, Ethylidene Malonitriles, and Allyltributylstannane2010

    • Author(s)
      Shirong Lu, Tienan Jin, Ming Bao, Yoshinori Yamamoto
    • Journal Title

      Organic Letters

      Volume: 12 Pages: 864-866

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene2010

    • Author(s)
      Zhibao Huo, Iliya D. Gridnev, Yoshinori Yamamoto
    • Journal Title

      The Journal of Organic Chemistry 75

      Pages: 1266-1270

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Gold-catalyzed Synthesis of Isoquinolines via Intramolecular Cyclization of 2-Alkynyl Benzyl Azides2009

    • Author(s)
      Nishina Naoko, Yamamoto Yoshinori
    • Journal Title

      Tetrahedron

      Volume: 65 Pages: 1799-1808

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Gold-catalyzed Synthesis of Isoquinolines via Intramolecular Cyclization of 2-Alkynyl Benzyl Azides2009

    • Author(s)
      Huo Zhibao, Yamamoto Yoshinori
    • Journal Title

      Tetrahedron Lett

      Volume: 50 Pages: 3651-3653

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Alkyne Activation with Bronsted Acids, Iodine, or Gold Complexes, and its Fate Leading to Synthetic Application2009

    • Author(s)
      Yamamoto Yoshinori, Gridnev Ilya D, Patil Nitin T, Jin Tienan
    • Journal Title

      Chem. Commun

      Pages: 5075-5087

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Gold-catalyzed hydrofunctionalization of allenes with nitrogen and oxygen nucleophiles and its mechanistic insight2009

    • Author(s)
      Naoko Nishina, Yoshinori Yamamoto
    • Journal Title

      Tetrahedron 65

      Pages: 1799-1808

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbocycle Synthesis through Facile and Efficient Palladium-Catalyzed Allylative Dearomatization of Naphthalene and Phenanthrene Allyl Chlorides2008

    • Author(s)
      Lu Shirong, Xu Zhanwei, Bao Ming, Yamamoto Yoshonori
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 47 Pages: 4366-4369

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Gold-catalyzed Intermolecular Hydroalkoxylation of Allenes : Difference in Mechanism between Hydroalkoxylation and Hydroamination2008

    • Author(s)
      Nishina Naoko, Yamamoto Yoshinori
    • Journal Title

      Tetrahedron Lett

      Volume: 49 Pages: 4908-4911

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Gold-catalyzed Synthesis of Polycyclic Enones from Carbon Tethered 1, 3-Enynyl Carbonyls via Tandem Heteroenyne Metathesis and Nazarov Reaction2008

    • Author(s)
      Jin Tienan, Yamamoto Yoshinori
    • Journal Title

      Org. Lett

      Volume: 10 Pages: 3137-3139

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Intramolecular Hydroamination of Alkynes in the Presence of a Catalytic System Consisting of Pd(0)-Methyl Norphos (or Tolyl Renorphos)-Benzoic Acid2008

    • Author(s)
      Narsireddy Meda, Yamamoto Yoshinori
    • Journal Title

      J. Org. Chem

      Volume: 73 Pages: 9698-9709

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chirality Transfer in Gold-Catalyzed Carbothiolation of o-Alkynylphenyl 1-Arylethyl Sulfides2008

    • Author(s)
      Nakamura Itaru, Sato Takuma, Terada Masahiro, Yamamoto Yoshinori
    • Journal Title

      Org. Lett

      Volume: 10 Pages: 2649-2651

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Intramolecular Hydroamination of Alkynes in the Presence of a Catakyst System Consisting of Pd (O)-Methyl Norphos (or Tolyl Renorphos)-Benzoic Acid2008

    • Author(s)
      Meda Narsireddy, Yoshinori Yamamoto
    • Journal Title

      J. Org. Chem. 73

      Pages: 9698-9709

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination2008

    • Author(s)
      Naoko Nishina, Yoshinori Yamamoto
    • Journal Title

      Tetrahedron Lett. 49

      Pages: 4908-4911

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] From Molecular Catalysts to Nano-structured Materials Skeleton Catalysts2011

    • Author(s)
      山本嘉則
    • Organizer
      16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2011-07-24
    • Related Report
      2010 Final Research Report
  • [Presentation] From Molecular Catalysts to Nano-structured Materials Skeleton Catalysts2011

    • Author(s)
      山本嘉則
    • Organizer
      16th IUPAC International Symposium on Organo metallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Shanghai, China(招待講演)
    • Year and Date
      2011-07-24
    • Related Report
      2010 Annual Research Report
  • [Presentation] シグマおよびパイ配位性ルイス酸を用いる分子変換2010

    • Author(s)
      山本嘉則
    • Organizer
      日本薬学会進歩のシンポ
    • Place of Presentation
      名古屋
    • Year and Date
      2010-11-01
    • Related Report
      2010 Final Research Report
  • [Presentation] σ-とπ-配位性ルイス酸の有機合成への応用2010

    • Author(s)
      山本嘉則
    • Organizer
      日本学術振興会第116委員会講演会
    • Place of Presentation
      学士会会館
    • Year and Date
      2010-06-08
    • Related Report
      2010 Final Research Report
  • [Presentation] π電子親和性ルイス酸を用いる新規分子変換反応2009

    • Author(s)
      山本嘉則
    • Organizer
      第36回有機反応懇談会
    • Place of Presentation
      関西学院大学、神戸三田キャンパス
    • Year and Date
      2009-08-03
    • Related Report
      2010 Final Research Report
  • [Presentation] π電子親和性ルイス酸を用いる新規分子変換反応2009

    • Author(s)
      山本嘉則
    • Organizer
      第21回万有札幌シンポジウム
    • Place of Presentation
      北海道厚生年金会館
    • Year and Date
      2009-07-04
    • Related Report
      2010 Final Research Report
  • [Presentation] コイネージメタル触媒を用いる新規分子変換反応2009

    • Author(s)
      山本嘉則
    • Organizer
      日本薬学会129年会
    • Place of Presentation
      国立京都会館
    • Year and Date
      2009-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] Coinage Metalsを触媒とする新規分子変換反応2009

    • Author(s)
      山本嘉則
    • Organizer
      有機合成ニュートレンド2009
    • Place of Presentation
      有機合成化学協会関西支部、大阪科学技術センター
    • Year and Date
      2009-02-03
    • Related Report
      2010 Final Research Report
  • [Presentation] From σ-to π-Electrophilic Lewis Acids2009

    • Author(s)
      山本嘉則
    • Organizer
      Application to Selective Organic Transformations
    • Place of Presentation
      Univ. York, Univ. Belfast, Durham Univ. UK
    • Related Report
      2010 Final Research Report
  • [Presentation] π-Electrophilic Lewis Acids Catalyzed New transformations2009

    • Author(s)
      山本嘉則
    • Organizer
      International Conference in celebration of the Official Opening of the School of Physical and Methematical Science Building
    • Place of Presentation
      NANYANG TECHNOLOGICAL UNIVERSITY, Singapore
    • Related Report
      2010 Final Research Report
  • [Presentation] 金触媒を用いる新規分子変換反応2008

    • Author(s)
      山本嘉則
    • Organizer
      平成20年前期有機合成化学講習会
    • Place of Presentation
      日本薬学会長井記念ホール
    • Year and Date
      2008-06-18
    • Related Report
      2010 Final Research Report
  • [Presentation] Coinage Metal Catalyzed New Reactions2008

    • Author(s)
      山本嘉則
    • Organizer
      Gordon Research Conference
    • Place of Presentation
      Bryant University, USA
    • Related Report
      2010 Final Research Report
  • [Presentation] Coinage metal catalyzed new reactions2008

    • Author(s)
      山本嘉則
    • Organizer
      IASOC (ISCHIA ADVANCED SCHOOL OF ORGANIC CHEMISTRY
    • Place of Presentation
      イタリア
    • Related Report
      2010 Final Research Report
  • [Book] Transition Metal Catalyzed Cyclization Reactions of functionalized Alkenes, Alkynes, and Allenes, in Handbook of Cyclization Reactions2010

    • Author(s)
      Patil Nitin T, Yamamoto Yoshinori
    • Publisher
      Wiley-VCH, Weinheim
    • Related Report
      2010 Final Research Report
  • [Book] Metal-catalyzed intramolecular heteroatom (X)→carbon (C)functional group migration reactions involving additions of X-Y bonds across alkynes2010

    • Author(s)
      Patil Nitin T., Kavthe R. D, Yamamoto Yoshinori
    • Publisher
      Advances in Heterocyclic Chemistry
    • Related Report
      2010 Final Research Report
  • [Book] Handbook of Cyclization Reactions, Volume 12010

    • Author(s)
      Nitin Patil, Yoshinori Yamamoto, Ed.by Shengming Ma
    • Total Pages
      69
    • Publisher
      Wiley-VCH, Weinheim
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.wpi-aimr.tohoku.ac.jp/yamamoto/index.html

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.wpi-aimr.tohoku.ac.jp/~yamamoto/

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.wpi-aimr.tohoku.ac.jp/~yamamoto/

    • Related Report
      2009 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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