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Development and Efficient Production of Organosulfur and Organophosphorus Compounds by Transition Metal Catalyzed Method

Research Project

Project/Area Number 21229001
Research Category

Grant-in-Aid for Scientific Research (S)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTohoku University

Principal Investigator

YAMAGUCHI Masahiko  東北大学, 薬学研究科(研究院), 教授 (30158117)

Co-Investigator(Renkei-kenkyūsha) AN Zenjian  東北大学, 大学院薬学研究科, 研究助教 (80532176)
SHIGENO Masanori  東北大学, 大学院薬学研究科, 助教 (30571921)
ICHINOSE Wataru  東北大学, 大学院薬学研究科, 研究助教 (00636409)
SAITO Nozomi  東北大学, 大学院薬学研究科, 研究助教 (40636411)
LI Guanzou  東北大学, 大学院薬学研究科, 研究助教 (90714824)
Project Period (FY) 2009-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥206,700,000 (Direct Cost: ¥159,000,000、Indirect Cost: ¥47,700,000)
Fiscal Year 2013: ¥36,400,000 (Direct Cost: ¥28,000,000、Indirect Cost: ¥8,400,000)
Fiscal Year 2012: ¥36,400,000 (Direct Cost: ¥28,000,000、Indirect Cost: ¥8,400,000)
Fiscal Year 2011: ¥36,400,000 (Direct Cost: ¥28,000,000、Indirect Cost: ¥8,400,000)
Fiscal Year 2010: ¥36,400,000 (Direct Cost: ¥28,000,000、Indirect Cost: ¥8,400,000)
Fiscal Year 2009: ¥61,100,000 (Direct Cost: ¥47,000,000、Indirect Cost: ¥14,100,000)
Keywords有機ヘテロ元素化合物 / 遷移金属触媒 / 平衡制御 / 非平衡熱力学系 / 省エネルギー / ヘテロ元素化合物 / 有機合成化学 / 平衡移動 / ナノ粒子 / 遷移金属 / イオウ / リン / 触媒 / 有機合成 / 不均一系反応場 / 均一系
Outline of Final Research Achievements

Conventional synthetic methods for organoheteroatom compounds used for drugs and materials often involve use of large amount of energy and resources. Activation of reactants is generally conducted by highly reactive reagents, which is accompanied by the formation of large amounts of waste materials. It is then highly desirable to develop efficient synthetic methods for the production of useful organoheteroatom compounds.
This research is conducted to develop efficient catalysts and equilibrium control methods for such purpose. With regard to the synthesis of organosulfur and organophosphorus compounds, followings were examined: 1) development of active catalysts; 2) development of catalytic equilibrium control methods; 3) systematic synthesis of heterocyclic compounds; 4) development of novel drugs and materials; 5) transition-metal-catalyzed regeneration of rough materials.

Assessment Rating
Verification Result (Rating)

A

Report

(6 results)
  • 2015 Research Progress Assessment (Verification Result) ( PDF )
  • 2014 Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (49 results)

All 2015 2014 2013 2012 2011 2010 Other

All Journal Article (34 results) (of which Peer Reviewed: 34 results,  Open Access: 5 results,  Acknowledgement Compliant: 3 results) Presentation (15 results) (of which Invited: 15 results)

  • [Journal Article] Synthesis of Thiiranes by Rhodium-catalyzed Sulfur Addition Reaction to Reactive Alkenes2015

    • Author(s)
      M. Arisawa, T. Ichikawa and M. Yamaguchi
    • Journal Title

      Chem. Commun.

      Volume: in press

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Helicene-grafted Silica Nanoparticles Capture Hetero-double-helix Intermediates During Self-assembly Gel Formation2015

    • Author(s)
      M. Miyagawa and M. Yamaguchi
    • Journal Title

      Chem. Eur. J.

      Volume: in press

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed 2-Methylthiolation Reaction of Thiazoles/Oxazoles Using 2-(Methylthio)Thizole2015

    • Author(s)
      M. Arisawa, Y. Nihei and M. Yamaguchi
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 5 Pages: 939-949

    • DOI

      10.3987/com-15-13193

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Palladium-Catalyzed Addition Reaction of Aroyl/Heteroaroyl Acid Anhydrides to Norbornenes2014

    • Author(s)
      M. Arisawa, S. Tanii and M. Yamaguchi
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 96 Pages: 15267-15270

    • DOI

      10.1039/c4cc07759h

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Molecular Function of Counting the Numbers 1 and 2 Exhibited by a Sulfonamidohelicene Tetramer2014

    • Author(s)
      Masanori Shigeno, Yo Kushida, Yuta Kobayashi, Masahiko Yamaguchi
    • Journal Title

      Chemistry A European Journal

      Volume: 20 Issue: 40 Pages: 12759-12762

    • DOI

      10.1002/chem.201403358

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Aminomethylenehelicene Oligomers Possessing Flexible Two-atom Linker Form a Stimuli-Responsive Double-Helix in Solution2014

    • Author(s)
      Masanori Shigeno, Masahiko Sato, Yo Kushida, Masahiko Yamaguchi
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 3 Issue: 7 Pages: 797-804

    • DOI

      10.1002/ajoc.201402065

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Heating/Cooling Stimulus Induces Three-State Molecular Switching of Pseudoenantiomeric Aminomethylenehelicene Oligomers: Reversible Nonequilibrium Thermodynamic Processes2014

    • Author(s)
      Masanori Shigeno, Yo Kushida, Masahiko Yamaguchi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 22 Pages: 7972-7980

    • DOI

      10.1021/ja502009f

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis, Double-Helix Formation, and Higher-Assembly Formation of Chiral Polycyclic Aromatic Compounds : Conceptual Development of Polyketide Aldol Synthesis2014

    • Author(s)
      Masahiko Yamaguchi, Masanori Shigeno, Nozomi Saito, Koji Yamamoto
    • Journal Title

      The Chemical Record

      Volume: 14 Issue: 1 Pages: 15-27

    • DOI

      10.1002/tcr.201300014

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Rhodium-catalyzed Synthesis of Unsymmetrical Di (Aryl/Heteroaryl) Methanes Using Aryl/Heteroarylmethyl Ketons via CO-C Bond Cleavage2014

    • Author(s)
      G. Li, M. Arisawa and M. Yamaguchi
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 33 Pages: 4328-4330

    • DOI

      10.1039/c4cc00816b

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent2013

    • Author(s)
      M. Arisawa, G. Li, M. Yamaguchi,
    • Journal Title

      Tetrahedron Lett.,

      Volume: 54 Issue: 10 Pages: 1298-1301

    • DOI

      10.1016/j.tetlet.2012.12.107

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Synthesis of Benzofurans by the Reaction of Ketones and O-Difluoeobenzenes2012

    • Author(s)
      M. Arisawa, S. Nakane, M. Kuwajima, M. Yamaguchi
    • Journal Title

      Heterocycles

      Volume: 86 Issue: 2 Pages: 1103-1118

    • DOI

      10.3987/com-12-s(n)57

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and Sulfur/Organopolysulfides2012

    • Author(s)
      M. Arisawa, T. Ichikawa, M. Yamaguchi
    • Journal Title

      Org. Lett.,

      Volume: 14 Pages: 5318-5321

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Arylthiolation Reaction of Nitroalkanes, Diethyl Malonate, and 1,2-Diphenylethanone with Diaryl Disulfides: Control of Disfavored Equilibrium Reaction2012

    • Author(s)
      M. Arisawa, Y. Nihei, M. Yamaguchi
    • Journal Title

      Tetrahedron Lett.,

      Volume: 53 Issue: 43 Pages: 5729-5732

    • DOI

      10.1016/j.tetlet.2012.07.132

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Acyl-Transfer Reaction between Benzyl Ketones and Thioesters: Synthesis of Unsymmetric Ketones by Ketone CO-C Bond Cleavage and Intermolecular Rearrangement2012

    • Author(s)
      M. Arisawa, M. Kuwajima, F. Toriyama, G. Li, M. Yamaguchi
    • Journal Title

      Org. Lett.,

      Volume: 14 Issue: 14 Pages: 3804-3807

    • DOI

      10.1021/ol3017148

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Opitical Resolution of Aromatic Alcohols Using Silica Nanoparticles Grafted with Helicene2012

    • Author(s)
      W. Ichinose, M. Miyagawa, Z. An, M. Yamaguchi
    • Journal Title

      Org. Lett.,

      Volume: 14 Issue: 12 Pages: 3123-3125

    • DOI

      10.1021/ol301206r

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two-Component Fibers/Gels and Vesicles Formed from Hetero-Double-Helices of Pseudoenantiomeric Ethynylhelicene Oligomers with Branched Side Cheins2012

    • Author(s)
      N. Saito, M. Shigeno, M. Yamaguchi
    • Journal Title

      Chem. Eur. J.,

      Volume: 18 Issue: 29 Pages: 8994-9004

    • DOI

      10.1002/chem.201200280

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Recognition in Aggregation of Gold Nanoparticles Grafted with Helicenes2012

    • Author(s)
      Z. An, M. Yamaguchi
    • Journal Title

      Chem. Commun.,

      Volume: 48 Issue: 59 Pages: 7383-7385

    • DOI

      10.1039/c2cc32735j

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formation of Organic Gel-Loquid Two-Layar Systems using Diffusion-Controlled Gelation with a Helicene Derivative2012

    • Author(s)
      M. Shigeno, M. Yamaguchi
    • Journal Title

      Chem. Commun.,

      Volume: 48 Issue: 49 Pages: 6139-6141

    • DOI

      10.1039/c2cc31977b

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Cleavage Reaction of Aryl Methyl Ethers with Thioesters2012

    • Author(s)
      M. Arisawa, Y. Nihei, T. Suzuki, M. Yamaguchi
    • Journal Title

      Org. Lett.,

      Volume: 14 Issue: 3 Pages: 855-857

    • DOI

      10.1021/ol2033724

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Equilibrium Shift in the Rhodium-catalyzed Acyl Transfer Reactions2011

    • Author(s)
      M. Arisawa, Y. Igarashi, H. Kobayashi, T.Yamada, K. Bando, T. Ichikawa, M. Yamaguchi
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 40 Pages: 7846-7859

    • DOI

      10.1016/j.tet.2011.07.031

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formation of double helix self-assembled monolayers of ethynylhelicene oligomer disulfides on gold surfaces2011

    • Author(s)
      K.Yamamoto, H.Sugihara, R.Amemiya, H.Aikawa, Z.An, M.Yamaguchi, M.Mizukami, K.Kurihara
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 33 Pages: 5972-5978

    • DOI

      10.1016/j.tet.2011.06.024

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed Phenylthiolation Reaction of Heteroaromatic Compounds using α-(phenylthio)isobutyrophenone2011

    • Author(s)
      M. Arisawa, F. Toriyama, M. Yamaguchi
    • Journal Title

      Tetrahedron Lett.,

      Volume: 52 Issue: 18 Pages: 2344-2347

    • DOI

      10.1016/j.tetlet.2011.02.077

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Transformation of Organosulfur Compounds to Organophosphorus Compounds: Rhodium-catalyzed Synthesis of 1-alkynylphosphine Sulfides and Acylphosphine Sulfides2011

    • Author(s)
      M. Arisawa, T. Watanabe, M. Yamaguchi
    • Journal Title

      Tetrahedron Lett.,

      Volume: 52 Issue: 18 Pages: 2410-2412

    • DOI

      10.1016/j.tetlet.2011.02.112

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed α-Methylthiolation Reaction of Unactivated Ketones Using 1,2-Diphenyl-2-methylthio-1-ethanone for the Methylthio Transfer Reagent2011

    • Author(s)
      M. Arisawa, F. Toriyama, M. Yamaguchi
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 12 Pages: 2305-2312

    • DOI

      10.1016/j.tet.2011.01.071

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed Carbothiolation Reaction of 1-alkylthio-1-alkynes2011

    • Author(s)
      M. Arisawa, Y. Igarashi, Y. Tagami, M. Yamaguchi, C.Kabuto
    • Journal Title

      Tetrahedron Lett.,

      Volume: 52 Issue: 8 Pages: 920-922

    • DOI

      10.1016/j.tetlet.2010.12.065

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An Activated Catalyst RhH(PPh3)4-dppe-Me2S2 for α-Methylthiolation of α-Phenyl Ketones2011

    • Author(s)
      M. Arisawa, F. Toriyama, M. Yamaguchi
    • Journal Title

      Heteroatom Chem.,

      Volume: 22 Pages: 18-23

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] AnActivated Catalyst RhH(PPh_3)_4-dppe-Me_2S_2 for α-Methylthiolation of α-Phenyl Ketones2011

    • Author(s)
      M.Arisawa, F.Toriyama, M.Yamaguchi
    • Journal Title

      Heteroatom Chem.

      Volume: 22 Pages: 18-23

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes2011

    • Author(s)
      M.Arisawa, Y.Igarashi, Y.Tagami, M.Yamaguchi, C.Kabuto
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 Pages: 920-922

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] RhCl_3-Catalyzed disulfide exchange reaction of insulfin and dithiodiglycolic acid2010

    • Author(s)
      M.Arisawa, M.Kuwajima, A.Suwa, M.Yamaguchi
    • Journal Title

      Heterocycles

      Volume: 80 Pages: 1239-1248

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide2010

    • Author(s)
      M.Arisawa, M.Yamaguchi
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 4840-4842

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of acylphosphine sulfides by rhodium-catalyzed reaction of acid fluorides and diphosphine disulfides2010

    • Author(s)
      M.Arisawa, T.Yamada, M.Yamaguchi
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 4957-4958

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Organothio Exchange Reaction of alpha α-Organothioketones with Disulfides2010

    • Author(s)
      M.Arisawa, F.Toriyama, M.Yamaguchi
    • Journal Title

      Chem.Phar.Bull.

      Volume: 58 Pages: 1349-1352

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors2010

    • Author(s)
      M.Arisawa, T.Yamada, M.Yamaguchi
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 6090-6092

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of o-(diphenylphosphinoyloxy)anilines by the rhodium-catalyzed reaction of nitroarenes and diphenylphosphine oxide2010

    • Author(s)
      M.Arisawa, M.Kuwajima, M.Yamaguchi
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 3116-3118

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] キラルヘリセンオリゴマーの合成と非平衡熱力学的反応2015

    • Author(s)
      山口雅彦
    • Organizer
      有機合成化学協会関西支部 有機合成2月セミナー
    • Place of Presentation
      大阪
    • Year and Date
      2015-02-03
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Equilibrium Crossing: Beyond Le Chatelier’s Principle2014

    • Author(s)
      山口雅彦
    • Organizer
      The 4th Joint Campus Asia Symposium
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-26 – 2014-11-27
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] キラルヘリセンオリゴマーの合成と非平衡熱力学的反応2014

    • Author(s)
      山口雅彦
    • Organizer
      第31回有機合成化学セミナー
    • Place of Presentation
      福岡
    • Year and Date
      2014-09-07
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Non-equilibrium Thermodynamic Properties of Synthetic Helicene Oligomers2014

    • Author(s)
      山口雅彦
    • Organizer
      シンポジウム モレキュラー・キラリティー2014
    • Place of Presentation
      仙台
    • Year and Date
      2014-06-07
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Non-equilibrium Thermodynamic Properties of Synthetic Helicene Oligomers2014

    • Author(s)
      山口雅彦
    • Organizer
      The 16th NOST Symposium
    • Place of Presentation
      アグラ(インド)
    • Year and Date
      2014-04-06
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Function of Novel Helical Substances: Synthesis of Self-assembled Gels

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      Institute of Chemistry Chinese Academy of Science
    • Place of Presentation
      北京、中国
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Function of Novel Helical Substances

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      National Taiwan Normal University
    • Place of Presentation
      台湾、中国
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Function of Novel Helical Substances

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      National Sun Yat-Sen University
    • Place of Presentation
      台湾、中国
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Hierarchical Buildup of Helicene-Containing Chiral Oligomers

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      13TH INTERNATIONAL SYMPOSIUM OF NATURAL PRODUCT CHEMISTRY
    • Place of Presentation
      カラチ、パキスタン
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] ラセン有機分子の合成と機能

    • Author(s)
      山口 雅彦
    • Organizer
      第1回大塚有機合成シンポジウム
    • Place of Presentation
      徳島
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Function of Novel Helical Compounds

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      The 15th Korea-Japan Seminar on Organic Chemistry
    • Place of Presentation
      Gyeongju, Korea
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Function of Novel Helical Substances

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      The 2nd DalianUniversity of Technology-Tohoku University Joint Symposium on Chemistry "Challenges in Environmental, Biomedical, and Materials Science & Technology"
    • Place of Presentation
      Dailen, China
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Hierarchical Buildup of Helicene-Containing Chiral Foldamers

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      BORDEAUX 2012 SYMPOSIUM ON FOLDAMERS
    • Place of Presentation
      BORDEAUX, France
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Function of Novel Helical Substances

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      Technische Universitat Munchen
    • Place of Presentation
      Munchen, Germany
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Hierarchical Buildup of Helicene-Containing Chiral Oligomers

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      The 2012 WPI-AIMR Annual Workshop in Sendai
    • Place of Presentation
      仙台
    • Related Report
      2011 Annual Research Report
    • Invited

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Published: 2009-04-01   Modified: 2019-07-29  

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