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2008 Fiscal Year Final Research Report

Development of New Molecular Transformations Based on Transition-Metal Catalyzed Cyanoboration of Carbon-Carbon Multiple Bonds

Research Project

  • PDF
Project/Area Number 17065012
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionKyoto University

Principal Investigator

SUGINOME Michinori  Kyoto University, 大学院・工学研究科, 教授 (60252483)

Project Period (FY) 2005 – 2008
Keywords有機合成化学
Research Abstract

高度に官能基化された有機ホウ素化合物の新しい合成法として,炭素置換基とホウ素置換基を不飽和有機化合物に同時に付加させる触媒反応であるカルボホウ素化反応を開発した。炭素-ホウ素結合の触媒的活性化を鍵段階とする反応として,シアノボランを用いるシアノホウ素化およびアルキニルボランを用いるアルキニルホウ素化反応を確立した。また,クロロボランをホウ素置換基の供給源とし,有機金属化合物を有機置換基の供給源として用いるカルボホウ素化反応も開発した。この反応では塩素-ホウ素結合の触媒的活性化が鍵段階となることもわかった。

  • Research Products

    (46 results)

All 2009 2008 2007 2006 2005 Other

All Journal Article (29 results) (of which Peer Reviewed: 29 results) Presentation (14 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Nickel-Catalyzed Ring-Opening Hydroacylation of Methylenecyclopropanes : Synthesis of γ,δ-Unsaturated Ketones from Aldehydes2009

    • Author(s)
      Taniguchi, H.; Ohmura, T.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 131

      Pages: 11298-11299

    • Peer Reviewed
  • [Journal Article] Easily Attachable and Detachable ortho-Directing Agent for Arylboronic Acids in Ruthenium-Catalyzed Aromatic C-H Silylation2009

    • Author(s)
      Ihara, H.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 131(22)

      Pages: 7502-7503

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed, Regio- and Stereoselective Hydroalkynylation of Methylenecyclopropanes with Retention of the Cyclopropane Ring, Leading to the Synthesis of 1-Methyl-1-Alkynylcyclopropanes2009

    • Author(s)
      Shirakura, M.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 131

      Pages: 5060-5061

    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of cis-β-Methyl- and Phenyl-Substituted Alkenylboranes via Platinum-Catalyzed Dehydrogenative Borylation2009

    • Author(s)
      Ohmura, T.; Takasaki, Y; Suginome, M.
    • Journal Title

      Angew. Chem., Int. Ed. 48

      Pages: 2372-2375

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Intramolecular Cyanoboration of Allenes Leading to the Regioselective Synthesis of β-Cyanoallylboranes2009

    • Author(s)
      Yamamoto, A.; Ikeda, Y.; Suginome, M.
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 5224-5226

    • Peer Reviewed
  • [Journal Article] B(OMe)_3 as a Nonacidic Iminium Ion Generator in Mannich- and Ugi-type Reactions2009

    • Author(s)
      Tanaka, Y.; Hidaka, K.; Hasui, T.; Suginome, M.
    • Journal Title

      Eur. J. Org. Chem.

      Pages: 1148-1151

    • Peer Reviewed
  • [Journal Article] Synthesis of Masked Haloareneboronic Acids via Iridium-Catalyzed Aromatic C-H Borylation with 1,8-Naphthalenediaminatoborane (danBH)2009

    • Author(s)
      Iwadate, N.; Suginome, M.
    • Journal Title

      J. Organomet. Chem. 694

      Pages: 1713-1717

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Regioselective Hydroalkynylation of Styrenes: Improved Catalyst System, Reaction Scope, and Mechanism2009

    • Author(s)
      Shirakura, M.; Suginome, M.
    • Journal Title

      Org. Lett. 17(3)

      Pages: 523-526

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Carboboration of Alkynes Using Chloroborane and Organozirconium Reagents2008

    • Author(s)
      Daini, M.; Suginome, M.
    • Journal Title

      Chem. Commun. (41)

      Pages: 5224-5226

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Addition of C-H Bonds of Terminal Alkynes to 1,3-Dienes and Styrenes2008

    • Author(s)
      Shirakura, M.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 130(16)

      Pages: 5410-5411

    • Peer Reviewed
  • [Journal Article] Diarylborinic Acid Derivatives as a Catalytic Iminium Ion Generator in the Mannich-type Reaction Using sec-Amines, Aldehydes, and Ketene Silyl Acetals2008

    • Author(s)
      Tanaka, T.; Hasui, T.; Suginome, M.
    • Journal Title

      Synlett (8)

      Pages: 1239-1242

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed trans- and cis-Carboboration of Alkynes Tethered to Chloroborane with Organozirconium Reagents: Ligand-Dependent Complementary Stereoselectivity2008

    • Author(s)
      Daini, M.; Yamamoto, A.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 2918-2919

    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed cis- and trans-Silaboration of Terminal Alkynes: Complementary Access to Stereo-Defined Trisubstituted Alkenes2008

    • Author(s)
      Ohmura, T.; Oshima, K.; Suginome, M.
    • Journal Title

      Chem. Commun.

      Pages: 1416-1418

    • Peer Reviewed
  • [Journal Article] Synthetic Application of Intramolecular Cyanoboration on the Basis of Removal and Conversion of a Tethering Group by Palladium-Catalyzed Retro-allylation2008

    • Author(s)
      Ohmura, T.; Awano, T.; Suginome, M.; Yorimitsu, H.; Oshima, K.
    • Journal Title

      Synlett (3)

      Pages: 423-427

    • Peer Reviewed
  • [Journal Article] Silylboranes Bearing Dialkylamino Groups on Silicon as Silylene Equivalents: Palladium-Catalyzed Regioselective Synthesis of 2,4-Disubstituted Siloles2008

    • Author(s)
      Ohmura, T.; Masuda, K.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 130(5)

      Pages: 1526-1527

    • Peer Reviewed
  • [Journal Article] A Mechanism for the Palladium-Catalyzed Regioselective Silaboration of Allene: A Theoretical Study2008

    • Author(s)
      Abe, Y.; Kuramoto, K.; Ehara, M.; Nakatsuji, H.; Suginome, M.; Murakami, M.; Ito, Y.
    • Journal Title

      Organometallics 27

      Pages: 1736-1742

    • Peer Reviewed
  • [Journal Article] Differentially Protected Benzenediboronic Acids: Divalent Cross-Coupling Modules for the Efficient Synthesis of Boron-Substituted Oligoarenes2008

    • Author(s)
      Noguchi, H.; Shioda, T.; Chou, C. -M.; Suginome, M.
    • Journal Title

      Org. Lett. 10(3)

      Pages: 377-380

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Asymmetric Silaborative C-C Cleavage of meso-Methylenecyclopropanes2007

    • Author(s)
      Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 129(12)

      Pages: 3518-3519

    • Peer Reviewed
  • [Journal Article] Acid-free, Aminoborane-mediated Ugi-type Reaction Leading to General Utilization of Secondary Amines2007

    • Author(s)
      Tanaka, T.; Hasui, T.; Suginome, M.
    • Journal Title

      Org. Lett. 9(22)

      Pages: 4407-4410

    • Peer Reviewed
  • [Journal Article] Boron-Masking Strategy for the Selective Synthesis of Oligoarenes via Iterative Suzuki-Miyaura Coupling2007

    • Author(s)
      Noguchi, H.; Hojo, K.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 758-759

    • Peer Reviewed
  • [Journal Article] Reductive Amination of Aldehydes Using Aminoboranes as Iminium Ion Generators2006

    • Author(s)
      Suginome, M.; Tanaka, M.; Hasui, T.
    • Journal Title

      Synlett

      Pages: 1047-1050

    • Peer Reviewed
  • [Journal Article] The Asymmetric Silaboration of Terminal Allenes Bearing a-Stereogenic Centers: Stereoselection Based on "Reagent Control2006

    • Author(s)
      Ohmura, T.; Suginome
    • Journal Title

      M. Org. Lett. 8

      Pages: 2503-2506

    • Peer Reviewed
  • [Journal Article] Ligand-Controlled, Complementary Stereoselectivity in the Platinum-Catalyzed Intramolecular Silaboration of Alkenes"2006

    • Author(s)
      Ohmura, T.; Furukawa, H.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 13366-13367

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Addition of Alkynylboranes to Alkynes2006

    • Author(s)
      Suginome, M.; Shirakura, M.; Yamamoto, A.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 14438-14439

    • Peer Reviewed
  • [Journal Article] Reactions of Cyanoboranes with a Palladium-PMe_3 Complex: Mechanism for the Catalytic Cyanoboration of Alkynes2006

    • Author(s)
      Suginome, M.; Yamamoto, A.; Sasaki, T.; Murakami M.
    • Journal Title

      Organometallics 25

      Pages: 2911-2913

    • Peer Reviewed
  • [Journal Article] Aminoboranes as New Iminium Ion Generators in Amination Reactions2006

    • Author(s)
      Suginome, M.
    • Journal Title

      Pure Appl. Chem. 78

      Pages: 1377-1387

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Addition of Cyanoboranes to Alkynes Leading to Regio- and Stereoselective Synthesis of β-Boryl-α,β-unsaturated Nitriles2005

    • Author(s)
      Suginome, M.; Yamamoto, A.; Murakami, M.
    • Journal Title

      Angew. Chem., Int. Ed. 44

      Pages: 2380-2382

    • Peer Reviewed
  • [Journal Article] Activation of Boron-Cyanide Bonds by Transition Metal Catalysts Leading to Intramolecular Cyanoboration of Alkynes2005

    • Author(s)
      Suginome, M.; Yamamoto, A.; Murakami, M.
    • Journal Title

      J. Organomet. Chem. 690

      Pages: 5300-5308

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed trans-Alkynylboration of Alkynes via Activation of a Boron-Chlorine Bond2005

    • Author(s)
      Yamamoto, A.; Suginome, M.
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 15706-15707

    • Peer Reviewed
  • [Presentation] Oligo- and Polyarenes with Well-Defined Primary and Secondary Structures: New Synthetic Strategies and Functions2009

    • Author(s)
      Suginome, M.
    • Organizer
      Catalysis and Fine Chemicals (C&FC)
    • Place of Presentation
      Seoul, Korea(招待講演)
    • Year and Date
      20091213-20091217
  • [Presentation] New Catalytic Accesses to Functionalized Organoboronic Acids for Organic Synthesis2009

    • Author(s)
      Suginome, M.
    • Organizer
      Nesmeyanov Conference
    • Place of Presentation
      Moscow, Russia(招待講演)
    • Year and Date
      20090928-20091002
  • [Presentation] Protection of Boronyl Groups for the Synthesis of Functionalized Organoboronic Acid Derivatives2009

    • Author(s)
      Suginome, M.
    • Organizer
      5th BASF Boron Conference
    • Place of Presentation
      Hyderabad, India(招待講演)
    • Year and Date
      20090303-20090304
  • [Presentation] Nickel-Catalyzed Addition of Alkyne C-H Bonds to 1,3-Dienes and Styrenes2008

    • Author(s)
      Suginome, M.
    • Organizer
      9th International Conference on Organic Reactions (ISOR)
    • Place of Presentation
      Chiayi, Taiwan(招待講演)
    • Year and Date
      20081120-20081123
  • [Presentation] Boron-Masking Strategy for Selective Synthesis of Oligoareneboronic Acids via Cross-Coupling Reactions2008

    • Author(s)
      Suginome, M.
    • Organizer
      13th International Conference on Boron Chemistry (IMEBORON-XIII)
    • Place of Presentation
      Platja d'Aro, Spain(招待講演)
    • Year and Date
      20080921-20080925
  • [Presentation] Asymmetric Catalysis on Asymmetrically Synthesized Helical Polymers Bearing Metal-Binding Sites2008

    • Author(s)
      Suginome, M.
    • Organizer
      20^<th> International Symposium on Chirality
    • Place of Presentation
      Geneva, Switzerland(招待講演)
    • Year and Date
      20080706-20080709
  • [Presentation] 含ホウ素σ結合活性化に基づいた新触媒反応の開発2008

    • Author(s)
      杉野目道紀
    • Organizer
      東京農工大分子触媒セミナー「多元素間結合切断のための戦略と分子変換反応への新しい展開」
    • Place of Presentation
      東京(招待講演)
    • Year and Date
      2008-11-15
  • [Presentation] 触媒的カルボホウ素化反応への取組みを起点とする新反応・新反応剤の開拓2008

    • Author(s)
      杉野目道紀
    • Organizer
      有機合成化学講習会
    • Place of Presentation
      東京(招待講演)
    • Year and Date
      2008-06-18
  • [Presentation] Efficient Accesses to Organoboron Compounds for Organic Synthesis2008

    • Author(s)
      Suginome, M.
    • Organizer
      China-Japan Joint Symposium on Functional Materials toward Future Catalysts
    • Place of Presentation
      Beijing, China(招待講演)
    • Year and Date
      2008-01-16
  • [Presentation] ホウ素の特性を活かした新しい精密有機合成2007

    • Author(s)
      杉野目道紀
    • Organizer
      東京工業大学理学研究流動機構シンポジウム
    • Place of Presentation
      東京(招待講演)
    • Year and Date
      2007-11-30
  • [Presentation] ホウ素化合物の「活性化」と「保護」を利用した精密有機合成2007

    • Author(s)
      杉野目道紀
    • Organizer
      2007年日本化学会西日本大会
    • Place of Presentation
      岡山(招待講演)
    • Year and Date
      2007-11-10
  • [Presentation] New Boron-Based Reagents and Reactions for Organic Synthesis2006

    • Author(s)
      Suginome, M.
    • Organizer
      2nd International BASF Boron Conference
    • Place of Presentation
      Tokyo(招待講演)
    • Year and Date
      20060926-20060927
  • [Presentation] Exploration of New Transition Metal Catalyzed Reactions for Organic Synthesis2006

    • Author(s)
      杉野目道紀
    • Organizer
      有機合成化学セミナー
    • Place of Presentation
      大沼(受賞講演)
    • Year and Date
      20060913-20060915
  • [Presentation] ホウ素化合物の遷移金属触媒反応2006

    • Author(s)
      杉野目道紀
    • Organizer
      第3回九州大学理学研究院化学部門研究セミナー
    • Place of Presentation
      福岡(招待講演)
    • Year and Date
      2006-01-14
  • [Book] Comprehensive Organometallic Chemistry III2007

    • Author(s)
      Suginome, M.
    • Total Pages
      869
    • Publisher
      Elsevier
  • [Remarks]

    • URL

      http://www.sbchem.kyoto-u.ac.jp/suginome-lab/

  • [Patent(Industrial Property Rights)] クロスカップリング反応を用いたオリゴマー化合物の合成方法2007

    • Inventor(s)
      杉野目道紀, 野口宙幹, 北條浩章
    • Industrial Property Rights Holder
      国立大学法人京都大学
    • Industrial Property Number
      特許・特願2008-505123
    • Filing Date
      2007-03-09

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Published: 2011-06-18   Modified: 2016-04-21  

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