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2013 Fiscal Year Final Research Report

Novel equilibrium control under transition-metal catalysis

Research Project

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Project/Area Number 22689001
Research Category

Grant-in-Aid for Young Scientists (A)

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

Principal Investigator

ARISAWA MIEKO  東北大学, 薬学研究科(研究院), 准教授 (50302162)

Project Period (FY) 2010-04-01 – 2014-03-31
Keywords平衡制御 / 触媒反応 / 有機イオウ化合物 / 切断再配列 / へテロ元素捕捉剤 / 平衡相関
Research Abstract

I found that transition-metal complexes could be used as catalyst for the synthesis and transformation of organosulfur compounds, and that a variety of reactions involving cleavage of heteroatom bonds such as C-S, C-F, C-C, C-O, S-S, P-P bonds were developed. The development of efficient catalysts, which decreases the activation energy of the reaction, provides equilibrium reactions, when the relative thermodynamic stabilities of the substrates and products are close. Then, equilibrium control methods using co-substrates and thermodynamically intermediate substrates were developed. Method employing the combination of transition-metal catalysis and equilibrium control can be generally used for the synthesis of organosulfur compounds.

  • Research Products

    (28 results)

All 2014 2013 2012 2011 2010 Other

All Journal Article (20 results) (of which Peer Reviewed: 20 results) Presentation (7 results) Remarks (1 results)

  • [Journal Article] Rhodium-catalyzed Synthesis of Unsymmetrical Di(aryl/heteroaryl)methanes Using Aryl/heteroarylmethyl Ketones via CO-C Bond Cleavage2014

    • Author(s)
      Guangzhe Li, Mieko Arisawa, Masahiko Yamaguchi
    • Journal Title

      Chemical Communication

      Volume: 50 Pages: 4328-4330

    • DOI

      10.1039/c4cc00816b

    • Peer Reviewed
  • [Journal Article] Synthesis of Unsymmetrical Polyfluorinated Diaryl Sulfides by Rhodium-catalyzed Aryl Exchange Reaction2013

    • Author(s)
      Mieko Arisawa, Takuya Ichikawa, Masahiko Yamaguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Pages: 4327-4329

    • DOI

      10.1016/j.tetlet.2013.06.021

    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed Synthesis and Reactions of N-Acylphthalimides2013

    • Author(s)
      Guangzhe Li, Mieko Arisawa, Masahiko Yamaguchi
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 2 Pages: 983-988

    • DOI

      10.1002/ajoc.201300094

    • 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)
      Mieko Arisawa, Guangzhe Li, and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Pages: 1298-1301

    • DOI

      10.1016/j.tetlet2012.12.107

    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and Sulfur/Organopolysulfides2012

    • Author(s)
      Mieko Arisawa, Takuya Ichikawa, and Masahiko Yamaguchi
    • Journal Title

      Organic Letters

      Volume: 14 Pages: 5318-5321

    • DOI

      10.1021/ol302497m

    • 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)
      Mieko Arisawa, Yuri Nihei, and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Pages: 5729-5732

    • DOI

      10.1016/j.tetlet.2012.07.132

    • 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)
      Mieko Arisawa, Manabu Kuwajima, Fumihiko Toriyama, Guangzhe Li, and Masahiko Yamaguchi
    • Journal Title

      Organic Letters

      Volume: 14 Pages: 3804-3807

    • DOI

      10.1021/ol3017148

    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed Synthesis of Benzofurans by the Reaction of Ketones and O-Difluorobenzenes2012

    • Author(s)
      Mieko Arisawa, Souichiro Nakane, Manabu Kuwajima, and Masahiko Yamaguchi
    • Journal Title

      Heterocycles

      Volume: 86 Pages: 1103-1118

    • DOI

      10.3987/COM-12-S(N)57

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Cleavage Reaction of Aryl Methyl Ethers with Thioesters2012

    • Author(s)
      Mieko Arisawa, Yuri Nihei, Takaaki Suzuki, and Masahiko Yamaguchi
    • Journal Title

      Organic Letters

      Volume: 14 Pages: 855-857

    • DOI

      10.1021/ol2033724

    • Peer Reviewed
  • [Journal Article] Equilibrium Shift in the Rhodium-Catalyzed Acyl Transfer Reactions2011

    • Author(s)
      Mieko Arisawa, Yui Igarashi, Haruki Kobayashi, Toru Yamada, Kentaro Bando, Takuya Ichikawa, and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 7846-7859

    • DOI

      10.1016/j.tet.2011.07.031

    • Peer Reviewed
  • [Journal Article] Synthesis and Substitution Reactions of 4(6)-Chlorodihydropyrimidines2011

    • Author(s)
      Hidetsura Cho, Yoshizumi Yasui, Satoshi Kobayashi, Eunsang Kwon, Mieko Arisawa, and Masahiko Yamaguchi
    • Journal Title

      Heterocycles

      Volume: 83 Pages: 1807-1818

    • DOI

      10.3987/COM-11-12244

    • Peer Reviewed
  • [Journal Article] Direct transformation of organosulfurcompounds to organophosphorus compounds : rhodium-catalyzed synthesis of 1-alkynylphosphinesulfides and acylphosphinesulfides2011

    • Author(s)
      Mieko Arisawa, Takuya Watanabe, and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Pages: 2410-2412

    • DOI

      10.1016/j.tetlet.2011.02.112

    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using α-(phenylthio)isobutyrophenone2011

    • Author(s)
      Mieko Arisawa, Fumihiko Triyama, and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Pages: 2344-2347

    • DOI

      10.1016/j.tetlet.2011.02.077

    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzedcarbothiolationreactionof1-al kylthio-1-alkynes2011

    • Author(s)
      Mieko Arisawa, Yui Igarashi, Yoko Tagami, Masahiko Yamaguchi, and Chizuko Cabuto
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Pages: 920-922

    • DOI

      10.1016/j.tetlet.2010.12.065

    • 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)
      Mieko Arisawa, Fumihiko Triyama, and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 2305-2312

    • DOI

      10.1016/j.tet.2011.01.071

    • Peer Reviewed
  • [Journal Article] An activated catalyst RhH(PPh_3)_4-dppe-Me_2S_2 for α-methylthiolation of α-phenyl ketones2011

    • Author(s)
      Mieko Arisawa, Fumihiko Triyama, and Masahiko Yamaguchi
    • Journal Title

      Heteroatom Chemistry

      Volume: 22 Pages: 18-23

    • DOI

      10.1002/hc.20650

    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatomacceptors2010

    • Author(s)
      Mieko Arisawa, Toru Yamada, and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 6090-6092

    • DOI

      10.1016/j.tetlet.2010.09.009

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

    • Author(s)
      Mieko Arisawa, Toru Yamada, and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 4957-4958

    • DOI

      10.1016/j.tetlet.2010.07.038

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

    • Author(s)
      Mieko Arisawa and Masahiko Yamaguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 4840-4842

    • DOI

      10.1016/j.tetlet.2010.07.040

    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed organothio exchange reaction of α-organothioketones with disulfides2010

    • Author(s)
      Mieko Arisawa, Fumihiko Triyama, and Masahiko Yamaguchi
    • Journal Title

      Chemical & Pharmaceutical Bulletin

      Volume: 58 Pages: 1349-1352

    • DOI

      10.1248/cpb.58.1349

    • Peer Reviewed
  • [Presentation] 芳香族/複素環エーテルから非対称芳香族/複素環スルフィドを合成するロジウム触媒反応2014

    • Author(s)
      有澤 美枝子
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Year and Date
      2014-03-28
  • [Presentation] 遷移金属触媒を用いる高周期へテロ元素化合物の合成2013

    • Author(s)
      有澤美枝子
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Year and Date
      2013-11-05
  • [Presentation] 有機ポリスルフィド/イオウ単体を用いるロジウム触媒芳香族フッ化物のチオ化反応2012

    • Author(s)
      有澤 美枝子
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2012-09-13
  • [Presentation] 芳香族メチルエーテルのロジウム触媒切断変換反応2012

    • Author(s)
      有澤 美枝子
    • Organizer
      第101回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2012-06-06
  • [Presentation] 有機イオウ・リン化合物の触媒的平衡制御合成2011

    • Author(s)
      有澤 美枝子
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Year and Date
      2011-11-07
  • [Presentation] 遷移金属触媒を用いる有機イオウ・リン化合物の多様な合成法の開発2011

    • Author(s)
      有澤 美枝子
    • Organizer
      第28回有機合成化学セミナー
    • Place of Presentation
      山形
    • Year and Date
      2011-09-01
  • [Presentation] Rhodium- and palladium-catalyzed synthesis of organophosphorus compounds using diphosphine disulfides and dioxides2010

    • Author(s)
      Mieko Arisawa
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2010-12-15
  • [Remarks]

    • URL

      http://www.pharm.tohoku.ac.jp/~sekkei/sekkei-j.shtml

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Published: 2015-07-16  

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