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2010 Fiscal Year Final Research Report

Cross-Coupling through Selective Cleavage of C-H and C-C Bonds

Research Project

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Project/Area Number 20350050
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

MIURA Masahiro  大阪大学, 工学研究科, 教授 (20183626)

Co-Investigator(Renkei-kenkyūsha) SATOH Tetsuya  大阪大学, 工学研究科, 准教授 (40273586)
HIRANO Koji  大阪大学, 工学研究科, 助教 (70532696)
Project Period (FY) 2008 – 2010
Keywords合成化学 / クロスカップリング / 炭素結合 / 遷移金属触媒 / パイ共役分子
Research Abstract

The coupling reaction of suitably functionalized aromatic and heteroaromatic substrates with aryl halides, alkenes, and alkynes proceeded effectively in the presence of a palladium or rhodium catalyst. Especially, aromatic carboxylic acids was found to undergo multi-coupling via C-H and C-C bond cleavages to afford structurally interesting pi-conjugated compounds. Furthermore, a number of C-H transformation reactions of aromatic compounds by using copper and nickel catalysts have been developed.

  • Research Products

    (50 results)

All 2011 2010 2009 2008

All Journal Article (44 results) Presentation (4 results) Book (2 results)

  • [Journal Article] Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes2011

    • Author(s)
      Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 76 Pages: 9548-9551

  • [Journal Article] Ruthenium-catalyzed Oxidative Alkenylation of Arenes via Regioselective C-H Bond Cleavage Directed by a Nitrogen-containing Group2011

    • Author(s)
      Hashimoto, Y.; Ueyama, T.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Lett

      Volume: 40 Pages: 1165-1166

  • [Journal Article] Palladium-catalyzed Direct Monoarylation of Thiophene-, Benzothiophene-, and Indoleacetic Acids through Regioselective C-H Bond Cleavage2011

    • Author(s)
      Takeda, D.; Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Lett

      Volume: 40 Pages: 1015-1017

  • [Journal Article] Copper-Catalyzed Oxidative Direct Cyclization of N-Methylanilines with Electron-Deficient Alkenes Using Molecular Oxygen2011

    • Author(s)
      Nishino, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 76 Pages: 6447-6451

  • [Journal Article] Copper-Mediated Annulative Direct Coupling of o-Alkynylphenols with Oxadiazoles : A Dehydrogenative Cascade Construction of Biheteroaryls2011

    • Author(s)
      Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 3076-3079

  • [Journal Article] Rhodium-catalyzed Oxidative Coupling of Benzylamines with Alkynes through Dehydrogenation and Dehydrogenative Cyclization2011

    • Author(s)
      Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Lett

      Volume: 40 Pages: 600-602

  • [Journal Article] Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydroxylamines2011

    • Author(s)
      Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 2860-2863

  • [Journal Article] Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group2011

    • Author(s)
      Mochida, S.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 76 Pages: 3024-3033

  • [Journal Article] Copper-Catalyzed Annulative Amination of ortho-Alkynylphenols with Hydroxylamines : Synthesis of 3-Aminobenzofurans by Umpolung Amination Strategy2011

    • Author(s)
      Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 2395-2397

  • [Journal Article] Synthesis of Highly Substituted Acenes through Rhodium-Catalyzed Oxidative Coupling of Arylboron Reagents with Alkynes2011

    • Author(s)
      Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 76 Pages: 2867-2874

  • [Journal Article] Synthesis of 1, 4-Diarylbuta-1, 3-dienes through Palladium-Catalyzed Decarboxylative Coupling of Unsaturated Carboxylic Acids2011

    • Author(s)
      Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Adv. Synth. Catal

      Pages: 294-307

  • [Journal Article] Direct Carbon-Hydrogen Bond Functionalization of Heterocyclic Compounds2011

    • Author(s)
      Hirano, K.; Miura, M.
    • Journal Title

      Synlett

      Volume: 353 Pages: 631-636

  • [Journal Article] Copper-Mediated Intermolecular Direct Biaryl Coupling2011

    • Author(s)
      Kitahara, M.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 2160-2162

  • [Journal Article] Ruthenium-Catalyzed Oxidative Vinylation of Heteroarene Carboxylic Acids with Alkenes via Regioselective C-H Bond Cleavage2011

    • Author(s)
      Ueyama, T.; Mochida, S.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 706-708

  • [Journal Article] Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions2011

    • Author(s)
      Miyasaka, M.; Hirano, K.; Satoh, T.; Kowalczyk, R.; Bolm, C.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 359-361

  • [Journal Article] Rhodium-Catalyzed Oxidative 1 : 1, 1 : 2, and 1 : 4 Coupling Reactions of Phenylazoles with Internal Alkynes through the Regioselective Cleavages of Multiple C-H Bonds2011

    • Author(s)
      Umeda, N.; Hirano, K.; Satoh, T.; Shibata, N.; Sato, H.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 76 Pages: 13-24

  • [Journal Article] Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed Ortho-Olefination and Decarboxylation of Benzoic Acids2010

    • Author(s)
      Mochida, S.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 12 Pages: 5776-5779

  • [Journal Article] Palladium-and Nickel-Catalyzed Direct Alkylation of Azoles with Unactivated Alkyl Bromides and Chlorides2010

    • Author(s)
      Yao, T.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Eur. J

      Volume: 16 Pages: 12307-12311

  • [Journal Article] Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis2010

    • Author(s)
      Satoh, T.; Miura, M.
    • Journal Title

      Chem. Eur. J

      Volume: 16 Pages: 11212-11222

  • [Journal Article] Oxidative Nickel-Air Catalysis in C-H Arylation : Direct Cross-Coupling of Azoles with Arylboronic Acids using Air as Sole Oxidant2010

    • Author(s)
      Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      ChemCatChem

      Volume: 2 Pages: 1403-1406

  • [Journal Article] Palladium-Catalyzed Direct Oxidative Alkenylation of Azoles2010

    • Author(s)
      Miyasaka, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 75 Pages: 5421-5424

  • [Journal Article] Transition-Metal-Catalyzed Regioselective Arylation and Vinylation of Carboxylic Acids2010

    • Author(s)
      Satoh, T.; Miura, M.
    • Journal Title

      Synthesis

      Volume: 20 Pages: 3395-3409

  • [Journal Article] Rhodium-catalyzed Oxidative Coupling/ Cyclization of Benzamides with Alkynes via C-H Bond Cleavage2010

    • Author(s)
      Mochida, S.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Lett

      Volume: 39 Pages: 744-746

  • [Journal Article] Nickel-Catalyzed Direct C-H Arylation and Alkenylation of Heteroarenes with Organosilicon Reagents2010

    • Author(s)
      Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49 Pages: 2202-2205

  • [Journal Article] Copper-Mediated Direct Cross-Coupling of 1, 3, 4-Oxadiazoles and Oxazoles with Terminal Alkynes2010

    • Author(s)
      Kitahara, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Eur. J

      Volume: 16 Pages: 1772-1775

  • [Journal Article] Synthesis ofα,ω-Diarylbutadienes and-Hexatrienes via Decarboxylative Coupling of Cinnamic Acids with Vinyl Bromides under Palladium Catalysis2010

    • Author(s)
      Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 12 Pages: 592-595

  • [Journal Article] Synthesis of Substituted Stilbenes via Direct Decarboxylative Coupling of Cinnamic Acids with Arylboronic Acids under Palladium Catalysis2010

    • Author(s)
      Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Lett

      Volume: 39 Pages: 68-69

  • [Journal Article] Rhodium/ Phosphine/ Amine-HBr Catalyst System for Highly Selective Cross-Cyclodimerization of Aryl-and Alkylalkynes : Efficient Access to Multisubstituted Naphthalene Derivatives2010

    • Author(s)
      Sakabe, K.; Tsurugi, H.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Eur. J

      Volume: 16 Pages: 445-449

  • [Journal Article] Synthesis of 2, 3-Diarylbenzo[ b] thiophenes via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling and Palladium-Catalyzed Decarboxylative Arylation2009

    • Author(s)
      Miyasaka, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Adv. Synth. Catal

      Volume: 351 Pages: 2683-2688

  • [Journal Article] Synthesis of Highly Substituted Naphthalene and Anthracene Derivatives by Rhodium-Catalyzed Oxidative Coupling of Arylboronic Acids with Alkynes2009

    • Author(s)
      Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 11 Pages: 5198-5201

  • [Journal Article] Fused Ring Construction around Pyrrole, Indole, and Related Compounds via Palladium-Catalyzed Oxidative Coupling with Alkynes2009

    • Author(s)
      Yamashita, M.; Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 74 Pages: 7481-7488

  • [Journal Article] Nickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl Bromides2009

    • Author(s)
      Matsuyama, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 11 Pages: 4156-4159

  • [Journal Article] Rhodium-Catalyzed Mono-and Divinylation of 1-Phenylpyrazoles and Related Compounds via Regioselective C-H Bond Cleavage2009

    • Author(s)
      Umeda, N.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 74 Pages: 7094-7099

  • [Journal Article] Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage2009

    • Author(s)
      Fukutani, T.; Umeda, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Chem. Commun

      Pages: 5141-5143

  • [Journal Article] Nickel-Catalyzed C-H Alkenylation and Alkylation of 1, 3, 4-Oxadiazoles with Alkynes and Styrenes2009

    • Author(s)
      Mukai, T.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 74 Pages: 6410-6413

  • [Journal Article] Synthesis of Functionalizedα-Pyrone and Butenolide Derivatives by Rhodium-Catalyzed Oxidative Coupling of Substituted Acrylic Acids with Alkynes and Alkenes2009

    • Author(s)
      Mochida, S.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      J. Org. Chem

      Volume: 74 Pages: 6295-6298

  • [Journal Article] Copper-Mediated Direct Arylation of 1, 3, 4-Oxadiazoles and 1, 2, 4-Triazoles with Aryl Iodides2009

    • Author(s)
      Kawano, T.; Yoshizumi, T.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 11 Pages: 3072-3075

  • [Journal Article] Synthesis of Condensed Heteroaromatic Compounds by Palladium-Catalyzed Oxidative Coupling o f Heteroarene Carboxylic Acids with Alkynes2009

    • Author(s)
      Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Org. Lett

      Volume: 11 Pages: 2337-2340

  • [Journal Article] Palladium-Catalyzed Three-Component 1 : 2 : 1 Coupling of Aryl Iodides, Alkynes, and Alkenes to Produce 1, 3, 5-Hexatriene Derivatives2009

    • Author(s)
      Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M.
    • Journal Title

      Adv. Synth. Catal

      Volume: 351 Pages: 1431-1436

  • [Journal Article] Fluorescent Diarylindoles by Palladium-Catalyzed Direct and Decarboxylative Arylations of Carboxyindoles2009

    • Author(s)
      Miyasaka, M.; Fukushima, A.; Satoh, T.; Hirano, K.; Miura, M.
    • Journal Title

      Chem. Eur. J

      Volume: 15 Pages: 3674-3677

  • [Journal Article] Synthesis of 2, 5-Diaryloxazoles through van Leusen Reaction and Copper-Mediated Direct Arylation2009

    • Author(s)
      Yosizumi, T.; Satoh, T.; Hirano, K.; Matsuo, D.; Orita, A.; Otera, J.; Miura, M.
    • Journal Title

      Tetrahedron Lett

      Volume: 50 Pages: 3273-3276

  • [Journal Article] Rhodium-Catalyzed and Coordination-Assisted Regioselective Alkenylation of Aromatic C-H Bonds with Terminal Silylacetylenes2009

    • Author(s)
      Katagiri, T.; Mukai, T.; Satoh, T.; Hirano, K.; Miura, M.
    • Journal Title

      Chem. Lett

      Volume: 38 Pages: 118-119

  • [Journal Article] Rhodium-Catalyzed Regioselective Arylation of Phenyazoles and Related Compounds with Arylboron Reagents via C-H Bond Cleavage2008

    • Author(s)
      Miyamura, S.; Tsurugi, H.; Satoh, T.; Miura, M.
    • Journal Title

      J. Organomet. Chem

      Volume: 693 Pages: 2438-2422

  • [Journal Article] Ligand Controlled Cross-Dimerization and-Trimerization of Alkynes under Nickel Cata lysis2008

    • Author(s)
      Matsuyama, N.; Tsutugi, H.; Satoh, T.; Miura, M.
    • Journal Title

      Adv. Synth. Catal

      Volume: 350 Pages: 2274-2278

  • [Presentation] Copper-Mediated Cross-Coupling via C-H Cleavage2011

    • Author(s)
      Miura, M.
    • Organizer
      Aachen-Osaka Joint Symposium : Biological and Chemical Approaches to Selective Processes
    • Place of Presentation
      RWTH Aachen University, Germany
    • Year and Date
      20110901-02
  • [Presentation] 遷移金属触媒を用いる直接的芳香族カップリングの新展開2010

    • Author(s)
      三浦雅博
    • Organizer
      第38回オルガノメタリックセミナー(触媒学会)
    • Place of Presentation
      大阪大学
    • Year and Date
      2010-11-22
  • [Presentation] 炭素.水素結合切断を経る触媒的芳香族カップリング2010

    • Author(s)
      三浦雅博
    • Organizer
      平成22年度後期有機合成化学講習会(有機合成化学協会)
    • Place of Presentation
      東京(日本薬学会長井記念館)
    • Year and Date
      2010-11-17
  • [Presentation] Catalytic Coupling Directed by Anionic Oxygen Functions via Cleavage of C-H and C-C Bonds2008

    • Author(s)
      Miura, M.
    • Organizer
      5^<th> Asian-European Symposium on Metal Mediated Efficient Organic Synthesis
    • Place of Presentation
      Obernai, France
    • Year and Date
      20080525-28
  • [Book] sp2-炭素-水素結合のアリール化およびアルケニル化,不活性結合・不活性分子の活性化2011

    • Author(s)
      佐藤哲也, 三浦雅博
    • Total Pages
      50-65
    • Publisher
      化学同人
  • [Book] Palladium-Catalyzed Direct Arylation Reactions, in Modern Arylation Methods2009

    • Author(s)
      Miura, M.; Satoh T.
    • Total Pages
      335-361
    • Publisher
      Wiley-VCH

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Published: 2013-07-31  

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