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2009 Fiscal Year Final Research Report

Development of New Catalytic Activities of Rhenium Complexes and Their Applications

Research Project

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Project/Area Number 19350049
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

TAKAI Kazuhiko  Okayama University, 大学院・自然科学研究科, 教授 (00144329)

Co-Investigator(Kenkyū-buntansha) KUNINOBU Yoichiro  岡山大学, 大学院・自然科学研究科, 助教 (40372685)
Project Period (FY) 2007 – 2009
Keywordsレニウム / マンガン / C-H結合活性化 / C-C結合切断 / 均一系錯体 / 触媒反応
Research Abstract

Compared to other metal elements, only a few synthetic reaction have been reported. Therefore, we started to explore the possibility of the use of rhenium complexes in organic synthesis. During this project we have found the following reactions using specific features of rhenium complexes. (1) Novel reactions based on the C(sp^2)-H bond activation with rhenium complexes. (2) Novel reactions based on the C-C bond cleavage of β-keto esters with rhenium complexes. (3) Rhenium catalyzed stereoselective [3+2]cycloaddition between β-keto esters and allenes. (4) Regioselective alkylation of phenols using olefins with a rhenium catalyst. (5) Manganese-catalyzed selective [2+2+2]cycloaddition leading to p-terphenyls

  • Research Products

    (53 results)

All 2010 2009 2008 2007 Other

All Journal Article (29 results) (of which Peer Reviewed: 28 results) Presentation (20 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Rhenium-and Manganese-Catalyzed Carbon-Carbon Bond Formation Using 1, 3-Dicarbonyl Compounds and Alkynes.2010

    • Author(s)
      Y. Kuninobu, A. Kawata, S.S. Yudha, H. Takata, M. Nishi, K. Takai
    • Journal Title

      Pure Appl. Chem. (in press)

    • Peer Reviewed
  • [Journal Article] Indium-Catalyzed Synthesis of Keto Esters from Cyclic 1, 3-Diketones and Alcohols and Application to the Synthesis of Seratrodast.2010

    • Author(s)
      Y. Kuninobu, A. Kawata, T. Noborio, S.-i. Yamamoto, T. Matsuki, K. Takata, K. Takai
    • Journal Title

      Chem. Asian J. Vol.5(in press)

    • Peer Reviewed
  • [Journal Article] Generation of Novel Nucleophilic Organometallic Species and Their Applications to Organic Synthesis.2010

    • Author(s)
      K. Takai
    • Journal Title

      J. Synth. Org. Chem. Vol.68,No.1

      Pages: 3-18

    • Peer Reviewed
  • [Journal Article] Rhenium-and Manganese-Catalyzed Synthesis of Aromatic Compounds from 1, 3-Dicarbonyl Compounds and Alkynes.2010

    • Author(s)
      Y. Kuninobu, M. Nishi, A. Kawata, H. Takata, Y. Hanatani, S.S. Yudha, A. Iwai, K. Takai
    • Journal Title

      J. Org. Chem. Vol.75,No.2

      Pages: 334-341

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Addition of β-Enamino Esters to Allenes.2009

    • Author(s)
      Y. Kuninobu, A. Yamashita, S.-i. Yamamoto, S.S. Yudha, K. Takai
    • Journal Title

      Synlett Vol.20,No.18

      Pages: 3027-3031

    • Peer Reviewed
  • [Journal Article] Rhenium-and Manganese-Catalyzed Insertion of Alkynes into a Carbon-Carbon Single Bond of Cyclic and Acyclic 1, 3-Dicarbonyl Compounds.2009

    • Author(s)
      Y. Kuninobu, A. Kawata, M. Nishi, S.S. Yudha, J.-i. Chen, K. Takai
    • Journal Title

      Chem. Asia J. Vol.4,No.9

      Pages: 1424-1433

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Regio-and Stereoselective Dimerization and Cyclotrimerization of Terminal Alkynes.2009

    • Author(s)
      A. Kawata, Y. Kuninobu, K. Takai
    • Journal Title

      Chem. Lett. Vol.38,No.8

      Pages: 836-837

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Regioselective Alkylation of Phenols.2009

    • Author(s)
      Y. Kuninobu, T. Matsuki, K. Takai
    • Journal Title

      J. Am. Chem. Soc. Vol.131,No.29

      Pages: 9914-9915

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Insertion of Nonpolar and Polar Unsaturated Molecules into an Olefinic C-H Bond.2009

    • Author(s)
      Y. Kuninobu, Y. Fujii, T. Matsuki, Y. Nishina, K. Takai
    • Journal Title

      Org. Lett. Vol.11,No.12

      Pages: 2711-2714

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Formation of Bicyclo[3. 3. 1]nonene Frameworks by a Reaction of Cyclic β-Keto Esters with Terminal Alkynes.2009

    • Author(s)
      Y. Kuninobu, J. Morita, M. Nishi, A. Kawata, K. Takai
    • Journal Title

      Org. Lett. Vol.11,No.12

      Pages: 2535-2537

  • [Journal Article] Rhenium-and Manganese-Catalyzed Insertion of Acetylenes into β-Keto Esters: Synthesis of 2-Pyranones.2008

    • Author(s)
      Y. Kuninobu, A. Kawata, M. Nishi, H. Takata, K. Takai
    • Journal Title

      Chem. Commun. No.47

      Pages: 6360-6362

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Synthesis of Stereodefined Cyclopentenes from β-Keto Esters and Aliphatic Allenes.2008

    • Author(s)
      S.S. Yudha, Y. Kuninobu, K. Takai
    • Journal Title

      Angew. Chem. Int. Ed. Vol.47,No.48

      Pages: 9318-9321

    • Peer Reviewed
  • [Journal Article] Reactions and Mechanistic Studies of Rhenium-Catalyzed Insertion ofα, β-Unsaturated Carbonyl Compounds into a C-H Bond.2008

    • Author(s)
      Y. Kuninobu, Y. Nishina, K. Okaguchi, M. Shouho, K. Takai
    • Journal Title

      Bull. Chem. Soc. Jpn. Vol.81,No.11

      Pages: 1393-1401

    • Peer Reviewed
  • [Journal Article] Synthesis of Cp-Re Complexes via Olefinic C-H Activation and Successive Formation of Cyclopentadienes.2008

    • Author(s)
      Y. Kuninobu, Y. Nishina, T. Matsuki, K. Takai
    • Journal Title

      J. Am. Chem. Soc. Vol.130,No.43

      Pages: 14062-14063

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Coupling of Propargyl Alcohols and Several Nucleophiles via Dehydration.2008

    • Author(s)
      Y. Kuninobu, H. Ueda, K. Takai
    • Journal Title

      Chem. Lett. Vol.37,No.8

      Pages: 878-879

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single Bond Cleavage.2008

    • Author(s)
      Y. Kuninobu, H. Takata, A. Kawata, K. Takai
    • Journal Title

      Org. Lett. Vol.10,No.14

      Pages: 3133-3135

    • Peer Reviewed
  • [Journal Article] Manganese-Catalyzed Construction of Tetrasubstituted Benzenes from 1, 3-Dicarbonyl Compounds and Terminal Acetylenes.2008

    • Author(s)
      Y. Kuninobu, M. Nishi, S.S. Yudha, K. Takai
    • Journal Title

      Org. Lett. Vol.10,No.14

      Pages: 3009-3011

    • Peer Reviewed
  • [Journal Article] Manganese-Catalyzed Synthesis of Hydantoin Derivatives from Terminal Alkynes and Isocyanates.2008

    • Author(s)
      Y. Kuninobu, K. Kikuchi, K. Takai
    • Journal Title

      Chem. Lett. Vol.37,No.7

      Pages: 740-741

    • Peer Reviewed
  • [Journal Article] Hydroarylation of Acetylenes, Acrylates and Isocyanates with Heteroaromatic Compounds under Rhenium Catalysis.2008

    • Author(s)
      Y. Kuninobu, K. Kikuchi, Y. Tokunaga, Y. Nishina, K. Takai
    • Journal Title

      Tetrahedron Vol.64,No.26

      Pages: 5974-5981

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Synthesis of Indene Derivatives via C-H Bond Activation.2008

    • Author(s)
      Y. Kuninobu, Y. Nishina, A. Kawata, M. Shouho, K. Takai
    • Journal Title

      Pure Appl. Chem. Vol.80,No.5

      Pages: 1149-1154

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Hydroamidation of Unactivated Terminal Alkynes: Synthesis of E-Enamides.2007

    • Author(s)
      S.S. Yudha, Y. Kuninobu, K. Takai
    • Journal Title

      Org. Lett. Vol.9,No.26

      Pages: 5609-5611

    • Peer Reviewed
  • [Journal Article] Copper(I)-and Gold(I)-Catalyzed Synthesis of 2, 4-Disubstituted Quinoline Derivatives from N-Aryl Propargyl Amines.2007

    • Author(s)
      Y. Kuninobu, Y. Inoue, K. Takai
    • Journal Title

      Chem. Lett. Vol.36,No.12

      Pages: 1422-1423

    • Peer Reviewed
  • [Journal Article] Indium-Catalyzed Retro-Claisen Condensation.2007

    • Author(s)
      A. Kawata, K. Takata, Y. Kuninobu, K. Takai
    • Journal Title

      Angew. Chem. Int. Ed. Vol.46,No.41

      Pages: 7793-7795

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed [2+2] Cycloadditions of Norbornenes with Internal and Terminal Acetylenes.2007

    • Author(s)
      Y. Kuninobu, P. Yu, K. Takai
    • Journal Title

      Chem. Lett. Vol.36,No.9

      Pages: 1162-1163

    • Peer Reviewed
  • [Journal Article] Manganese-Catalyzed Insertion of Aldehydes into a C-H Bond.2007

    • Author(s)
      Y. Kuninobu, Y. Nishina, T. Takeuchi, K. Takai
    • Journal Title

      Angew. Chem. Int. Ed. Vol.46,No.34

      Pages: 6518-6520

    • Peer Reviewed
  • [Journal Article] Rearrangement of Indene Skeletons under Mild Conditions.2007

    • Author(s)
      Y. Kuninobu, H. Ueda, A. Kawata, K. Takai
    • Journal Title

      J. Org. Chem. Vol.7,No.18

      Pages: 6749-6752

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Synthesis of Naphthalene Derivatives via Insertion of Aldehydes into a C-H Bond.2007

    • Author(s)
      Y. Kuninobu, Y. Nishina, K. Takai
    • Journal Title

      Tetrahedron Vol.63,No.29

      Pages: 8463-8468

    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Amidation of Heteroaromatic Compounds via C. H Bond Activation.2007

    • Author(s)
      Y. Kuninobu, Y. Tokunaga, K. Takai
    • Journal Title

      Chem. Lett. Vol.36,No.7

      Pages: 872-873

    • Peer Reviewed
  • [Journal Article] Rheniumand Gold-Catalyzed Coupling of Aromatic Aldehydes with Trimethyl(2-phenylethynyl)silane: Synthesis of Diethynylmethanes.2007

    • Author(s)
      Y. Kuninobu, E. Ishii, K. Takai
    • Journal Title

      Angew. Chem. Int. Ed. Vol.46,No.18

      Pages: 3296-3299

    • Peer Reviewed
  • [Presentation] Sequential Generation of Radical and Anionic Species Using Manganese Metal or Chromium(II).2009

    • Author(s)
      Kazuhiko Takai
    • Organizer
      4th Pacific Symposium on Radical Chemistry (PSRC4)
    • Place of Presentation
      Shanghai
    • Year and Date
      20091119-20091122
  • [Presentation] Rhenium-Catalyzed Regioselective Alkylation of Phenols.2009

    • Author(s)
      Takashi Matsuki, Yoichiro Kuninobu, Kazuhiko Takai
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOK-11)
    • Place of Presentation
      Kyoto
    • Year and Date
      20091109-20091113
  • [Presentation] Rhenium- and Manganese-Catalyzed Construction of 2-Pyranones fromβ-Keto Esters and Alkynes.2009

    • Author(s)
      Mitsumi Nishi, Atsushi Kawata, Hisatsugu Takata, Yoichiro Kuninobu, Kazuhiko Takai
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOK-11)
    • Place of Presentation
      Kyoto
    • Year and Date
      20091109-20091113
  • [Presentation] Atsuhiro Yamashita, Kazuhiko Takai, Rhenium-Catalyzed Reactions of Active Methylene Compounds with Allenes.2009

    • Author(s)
      Yoichiro Kuninobu, Salprima Yudha S.
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOK-11)
    • Place of Presentation
      Kyoto
    • Year and Date
      20091109-20091113
  • [Presentation] Rhenium-Catalyzed Insertion of Unsaturated Molecules into an Olefinic C-H Bond and its Application to the Synthesis of Cp-Re Complexes.2009

    • Author(s)
      Yoichiro Kuninobu, Takashi Matsuki, Yasuo Fujii, Yuta Nishina, Kazuhiko Takai
    • Organizer
      15th IUPAC Symposium on Organometallic Chemistry Directed toward Organic Synthesis (OMCOS15)
    • Place of Presentation
      Glasgow
    • Year and Date
      20090726-20090730
  • [Presentation] Rhenium- and Manganese-Catalyzed Carbon-Carbon Bond Formation Usingβ-Keto Esters.2009

    • Author(s)
      Kazuhiko Takai, Yoichiro Kuninobu, Atsushi Kawata, S.S. Yudha
    • Organizer
      15th IUPAC Symposium on Organometallic Chemistry Directed toward Organic Synthesis (OMCOS15)
    • Place of Presentation
      Glasgow
    • Year and Date
      20090726-20090730
  • [Presentation] レニウム及びマンガン触媒による合成反応の開発.2009

    • Author(s)
      高井和彦
    • Organizer
      有機合成ミニシンポジウム2009
    • Place of Presentation
      徳島大学長井記念ホール
    • Year and Date
      2009-10-17
  • [Presentation] 7族金属錯体触媒による合成反応の開発.2009

    • Author(s)
      高井和彦
    • Organizer
      Organic Syntheses Lectureship
    • Place of Presentation
      東京大学大学院薬学系研究科
    • Year and Date
      2009-07-03
  • [Presentation] 求核的な有機金属活性種の創製と合成への利用.2009

    • Author(s)
      高井和彦
    • Organizer
      2009年度有機合成化学協会協会賞受賞記念講演
    • Place of Presentation
      東京
    • Year and Date
      2009-02-20
  • [Presentation] Rhenium- and Manganese-Catalyzed Insertion of Acetylenes into a Carbon-Carbon Single Bond.2008

    • Author(s)
      Yoichiro Kuninobu, Atsushi Kawata, Mitsumi Nishi, Kazuhiko Takai
    • Organizer
      XXIII International Conference on Organometallic Chemistry (ICOMC2008)
    • Place of Presentation
      Rennes
    • Year and Date
      20080713-20080718
  • [Presentation] Annulation Reactions Based on C-H Bond Activation with a Rhenium Catalyst.2008

    • Author(s)
      Yoichiro Kuninobu, Yuta Nishina, Kazuhiko Takai
    • Organizer
      IUPAC 16th International Symposium on Homogeneous Catalysis (ISHC XVI)
    • Place of Presentation
      Florence
    • Year and Date
      20080706-20080711
  • [Presentation] Rhenium- and Manganese-Catalyzed Reactions of Aromatic Compounds with Aldehydes via C-H Bond Activation.2008

    • Author(s)
      Yoichiro Kuninobu, Yuta Nishina, Takahiro Takeuchi, Chie Nakagawa, Kazuhiko Takai
    • Organizer
      Third International Conference on Advanced Organic Synthesis Directed toward the Ultimate Efficiency and Practicability
    • Place of Presentation
      Otsu
    • Year and Date
      20080526-20080527
  • [Presentation] レニウム触媒を用いる炭素-炭素結合形成.2008

    • Author(s)
      高井和彦, 國信洋一郎
    • Organizer
      Organometallic Seminar XXXVI「分子触媒化学の新パラダイム」
    • Place of Presentation
      九州大学箱崎キャンパス
    • Year and Date
      2008-11-25
  • [Presentation] Rhenium- and Aniline-Catalyzed [3+2] Annulation of Aromatic Ketones andα, β-Unsaturated Esters.2007

    • Author(s)
      Kazuhiko Takai, Yoichiro Kuninobu, Yuta Nishina, Makoto Shouho
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2007
    • Place of Presentation
      Singapore
    • Year and Date
      20071216-20071221
  • [Presentation] Metal Activation by Addition of Catalytic Amounts of Different Metals - Synergistic Effects.2007

    • Author(s)
      Kazuhiko Takai
    • Organizer
      The 1st International Symposium on Synergy of Elements
    • Place of Presentation
      Tokyo
    • Year and Date
      20071112-20071113
  • [Presentation] Rhenium- and Manganese-Catalyzed Insertion of Aldehydes into a C-H Bond.2007

    • Author(s)
      Yuta Nishina, Takahiro Takeuchi, Chie Nakagawa, Yoichiro Kuninobu, Kazuhiko Takai
    • Organizer
      14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Nara
    • Year and Date
      20070802-20070806
  • [Presentation] Indium-Catalyzed Synthesis of Esters from 1, 3-Diketones and Alcohols via C-C Bond Cleavage.2007

    • Author(s)
      Atsushi Kawata, Kazumi Takata, Yoichiro Kuninobu, Kazuhiko Takai
    • Organizer
      14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Nara
    • Year and Date
      20070802-20070806
  • [Presentation] Rhenium-Catalyzed Insertion of Acetylenes into a Non-Strained Carbon-Carbon Single Bond.2007

    • Author(s)
      Yoichiro Kuninobu, Atsushi Kawata, Kazuhiko Takai
    • Organizer
      14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Nara
    • Year and Date
      20070802-20070806
  • [Presentation] Rhenium- and Aniline-Catalyzed One-Pot Annulation of Aromatic Ketones andα, β-Unsaturated Esters.2007

    • Author(s)
      Kazuhiko Takai, Yoichiro Kuninobu, Yuta Nishina, Makoto Shouho, Kayo Okaguchi
    • Organizer
      14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Nara
    • Year and Date
      20070802-20070806
  • [Presentation] レニウム触媒による炭素-水素活性化を基盤とする分子変換.2007

    • Author(s)
      高井和彦, 國信洋一郎
    • Organizer
      特定領域研究「高度分子変換」第3回公開シンポジウム
    • Place of Presentation
      北大
    • Year and Date
      20070618-20070619
  • [Book] Reductive Coupling Reactions Promoted by Low-valent Early Transition Metals and Lanthanoids2007

    • Author(s)
      Kazuhiko Takai
    • Total Pages
      39-73
    • Publisher
      Elsevier, Amsterdam
  • [Remarks]

    • URL

      http://achem.okayama-u.ac.jp/omc/index.html

  • [Patent(Industrial Property Rights)] シラフルオレン誘導体の製造方法2010

    • Inventor(s)
      國信洋一郎, 嬉野智也, 高井和彦
    • Industrial Property Rights Holder
      岡山大学
    • Industrial Property Number
      特許・特願2010-053857
    • Filing Date
      2010-03-10
  • [Patent(Industrial Property Rights)] アルキルフェノールの製造方法2009

    • Inventor(s)
      國信洋一郎, 松木崇, 高井和彦
    • Industrial Property Rights Holder
      岡山大学
    • Industrial Property Number
      特許・特願2009-58224
    • Filing Date
      2009-03-11

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

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