• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Catalytic Synthesis of Azulene-Containing pai-Conjugated Functionalized Materials

Research Project

Project/Area Number 26870389
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Synthetic chemistry
Research InstitutionOkayama University

Principal Investigator

Murai Masahito  岡山大学, 自然科学研究科, 助教 (40647070)

Research Collaborator TAKAMI KEISHI  
IBA SHINJI  
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsアズレン / 多環芳香族炭化水素 / ケイ素化 / 脱水素 / イリジウム / 炭素-水素結合活性化 / 檜山カップリング / ケイ素 / 刺激応答性 / 多環芳香族化合物 / 双極子 / 脱水素ケイ素化
Outline of Final Research Achievements

Azulenes, which show unique photophysical and redox properties derived from their unusual dipolar and π-electron polarizations, are promising components for the construction of advanced functional materials. In this study, we found the efficient dehydrogenative functionalization method of C-H bonds of azulenes with the production of hydrogen as the sole byproduct. The reaction occurred with excellent chemo- and regioselectivities to provide azulene derivatives functionalized at 2-position even without any directing groups. Effective conjugation through the 2-position of the azulene ring was demonstrated by the unique stimuli-responsiveness against acid-base reaction.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (50 results)

All 2016 2015 2014

All Journal Article (21 results) (of which Peer Reviewed: 21 results,  Acknowledgement Compliant: 11 results) Presentation (29 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results)

  • [Journal Article] Molybdenum-Catalyzed Stereospecific Deoxygenation of Epoxides to Alkenes2016

    • Author(s)
      Asako, Sobi; Sakae, Takahisa; Nakagiri, Takuya; Murai, Masahito; Takai, Kazuhiko
    • Journal Title

      Adv. Synth. Catal.

      Volume: 358 Issue: 24 Pages: 3966-3970

    • DOI

      10.1002/adsc.201600840

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium-Catalyzed Synthesis of Chiral Spiro-9-silabifluorenes via Dehydrogenative Silylation: Mechanistic Insights into the Construction of Tetraorganosilicon Stereocenters2016

    • Author(s)
      Masahito Murai, Yutaro Takeuchi, Kanae Yamauchi, Yoichiro Kuninobu, Kazuhiko Takai
    • Journal Title

      Chemistry -A European Journal

      Volume: 22 Issue: 17 Pages: 6048-6058

    • DOI

      10.1002/chem.201504718

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Direct Arylation of Azulene Based on the Regioselective C-H Bonds Activation2016

    • Author(s)
      Masahito Murai, Mayu Yanagawa, Masahiro Nakamura, Kazuhiko Takai
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: X Issue: 5 Pages: 629-635

    • DOI

      10.1002/ajoc.201600062

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Acceleration Effects of Phosphine Ligands on the Rhodium-Catalyzed Dehydrogenative Silylation and Germylation of Unactivated C(sp3)-H Bonds2015

    • Author(s)
      Masahito Murai, Hirotaka Takeshima, Haruka Morita, Yoichiro Kuninobu, Kazuhiko Takai
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 11 Pages: 5407-5414

    • DOI

      10.1021/acs.joc.5b00920

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed three-component coupling reactions of 2-(cyanomethyl)phenol, aryl halides, and carbon monoxide2015

    • Author(s)
      M. Murai, K. Okamoto, K. Miki, K. Ohe
    • Journal Title

      Tetrahedron

      Volume: online, 24-Apr-2015 Issue: 26-27 Pages: 1-6

    • DOI

      10.1016/j.tet.2015.04.049

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Ctalysis2015

    • Author(s)
      Takuya Nakagiri, Masahito Murai, Kazuhiko Takai
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 13 Pages: 3346-3349

    • DOI

      10.1021/acs.orglett.5b01583

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Synthesis of Benzosilolometallocenes via the Dehydrogenative Silylation of C(sp2)-H Bonds2015

    • Author(s)
      Masahito Murai, Koji Matsumoto, Yutaro Takeuchi, Kazuhiko Takai
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 12 Pages: 3102-3105

    • DOI

      10.1021/acs.orglett.5b01373

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Short Synthesis of [5]- and [7]Phenacenes with Silyl Groups at the Axis Positions2015

    • Author(s)
      David Roy, Hiroyuki Maekawa, Masahito Murai, Kazuhiko Takai
    • Journal Title

      Chemistry An Asian Journal

      Volume: 10 Issue: 11 Pages: 2518-2524

    • DOI

      10.1002/asia.201500700

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Iridium-Catalyzed Intermolecular Dehydrogenative Silylation of Polycyclic Aromatic Compounds without Directing Groups.2015

    • Author(s)
      Murai, M.; Takami, K.; Takai, K.
    • Journal Title

      Chemistry -A European Journal

      Volume: 21 Issue: 12 Pages: 4566-4570

    • DOI

      10.1002/chem.201406508

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Isolation and Structural Characterization of Geminal Di(iodozincio)methane Complexes Stabilized with Nitrogen Ligands.2015

    • Author(s)
      Nishida, Y.; Hosokawa, N.; Murai, M.; Takai, K.
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 1 Pages: 114-117

    • DOI

      10.1021/ja5114535

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhenium-Catalyzed anti-Markovnikov Addition Reaction of Methanetricarboxylates to Unactivated Terminal Acetylenes.2015

    • Author(s)
      Hori, S.; Murai, M.; Takai, K.
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 4 Pages: 1452-1457

    • DOI

      10.1021/ja5090755

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Transition Metal-Catalyzed Facile Access to 3,11-Dialkylfulminenes for Transistor Application2015

    • Author(s)
      M. Murai, H. Maekawa, S. Hamao, Y. Kubozono, D. Roy, K. Takai,
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 3 Pages: 708-711

    • DOI

      10.1021/ol503723j

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhenium-Catalysed Dehydrogenative Borylation of Primary and Secondary C(sp3)-H Bonds Adjacent to a Nitrogen Atom.2015

    • Author(s)
      Murai, M.; Omura, T.; Kuninobu, Y.; Takai, K.
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 22 Pages: 4583-4586

    • DOI

      10.1039/c4cc09508a

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Iridium-Catalyzed Dehydrogenative Silylation of Azulenes Based on the Regioselective C-H Bonds Activation.2015

    • Author(s)
      Murai, M.; Takami, K.; Takeshima, H; Takai, K.
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 7 Pages: 1798-1801

    • DOI

      10.1021/acs.orglett.5b00575

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Bismuth(III)-Catalyzed Dehydrative Etherification and Thioetherification of Phenolic Hydroxy Groups2014

    • Author(s)
      Masahito Murai, Kazuki Origuchi, Kazuhiko Takai
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 14 Pages: 3828-3831

    • DOI

      10.1021/ol501744g

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Modulating structure and properties in organic chromophores: influence of azulene as a building block2014

    • Author(s)
      Masahito Murai, Sung-Yu Ku, Neil D. Treat, Maxwell J. Robb, Michael L. Chabinyc, Craig J. Hawker
    • Journal Title

      Chemical Science

      Volume: 5 Issue: 10 Pages: 3753-3760

    • DOI

      10.1039/c4sc01623h

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Bismuth-Catalyzed Synthesis of PAHs with a Phenanthrene Backbone via Cyclization and Aromatization of 2-(2-Arylphenyl)vinyl Ethers2014

    • Author(s)
      Masahito Murai, Naoki Hosokawa, David Roy, Kazuhiko Takai
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 16 Pages: 4134-4137

    • DOI

      10.1021/ol5018273

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Conjugated oligomers incorporating azulene building blocks: seven- vs. five-membered ring connectivity2014

    • Author(s)
      Elizabeth Amir, Masahito Murai, Roey J. Amir, John S. Cowart, Michael L. Chabinyc and Craig J. Hawker
    • Journal Title

      Chemical Science

      Volume: 5 Issue: 11 Pages: 4483-4489

    • DOI

      10.1039/c4sc02210f

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Modulating the Properties of Azulene-Containing Polymers through Controlled Incorporation of Regioisomers2014

    • Author(s)
      Kazuhiko Tsurui, Masahito Murai, Sung-Yu Ku, Craig J. Hawker, Maxwell J. Robb
    • Journal Title

      Advanced Functional Materials

      Volume: 24 Issue: 46 Pages: 7338-7347

    • DOI

      10.1002/adfm.201402554

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhenium-Catalyzed Synthesis of 2H-1,2-Oxaphosphorin 2-Oxides via the Regio- and Stereoselective Addition Reaction of β-Keto Phosphonates with Alkynes.2014

    • Author(s)
      Murai, M.; Nakamura, M.; Takai, K.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 21 Pages: 5784-5787

    • DOI

      10.1021/ol502859w

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium-Catalyzed Dehydrogenative Germylation of C-H Bonds: New Entry to Unsymmetrically Functionalized 9-Germafluorenes.2014

    • Author(s)
      Murai, M.; Matsumoto, K.; Okada, R.; Takai, K.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 24 Pages: 6492-6495

    • DOI

      10.1021/ol503355q

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 遷移金属触媒による官能基化多環芳香族炭化水素の効率的な合成とその機能の開発2016

    • Author(s)
      村井征史
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] レニウム触媒による1,3-ケトエステルの末端アルキンへの逆Markovnikov型付加反応2016

    • Author(s)
      植村恵理香、堀駿介、村井征史、髙井和彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ロジウム触媒によるスピロシラビフルオレン合成における不斉発現メカニズムの解明2016

    • Author(s)
      竹内祐太朗、村井征史、髙井和彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis and properties of azulene-fused polycyclic aromatic hydrocarbons2015

    • Author(s)
      Masahito Murai, Shinji Iba, Kazuhiko Takai
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] アズレン骨格の組み込みによる多環芳香族炭化水素の物性の変化2015

    • Author(s)
      伊場真志、村井征史、髙井和彦
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-11-14
    • Related Report
      2015 Research-status Report
  • [Presentation] モリブデン触媒によるエポキシドの脱酸素反応を利用した立体選択的なオレフィン合成2015

    • Author(s)
      寒河江貴久、中桐卓也、浅子壮美、村井征史、髙井和彦
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-11-14
    • Related Report
      2015 Research-status Report
  • [Presentation] 窒素配位子により安定化されたgem-ビス(ヨードジンシオ) メタン錯体の単離と構造解析2015

    • Author(s)
      細川直輝、西田悠祐、村井征史、髙井和彦
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-11-14
    • Related Report
      2015 Research-status Report
  • [Presentation] ロジウム触媒による脱水素ケイ素化反応を利用する面性キラリティーを有するベンゾシロロメタロセンの合成2015

    • Author(s)
      松本浩志、村井征史、髙井和彦
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-11-14
    • Related Report
      2015 Research-status Report
  • [Presentation] Iridium-Catalyzed Intermolecular Dehydrogenative Silylation of Polycyclic Aromatic Compounds without Directing Groups2015

    • Author(s)
      Masahito Murai, Keishi Takami, Kazuhiko Takai
    • Organizer
      13th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2015-11-09
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Mechanistic insights into the construction of chiral spirosilabifluorenes via the rhodium-catalyzed dehydrogenative silylation2015

    • Author(s)
      Yutaro Takeuchi, Kanae Yamauchi, Masahito Murai, Kazuhiko Takai
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] Iridium-catalyzed intermolecular dehydrogenative silylation of polycyclic aromatic hydrocarbons based on the regio- and chemoselective C-H bond activation2015

    • Author(s)
      Masahito Murai, Keishi Takami, Kazuhiko Takai
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] レニウム触媒を用いる炭素求核剤の末端アルキンへの逆Markovnikov型付加反応2015

    • Author(s)
      堀駿介、村井征史、髙井和彦
    • Organizer
      第31回若手化学者のための化学道場
    • Place of Presentation
      淡路島
    • Year and Date
      2015-08-27
    • Related Report
      2015 Research-status Report
  • [Presentation] ロジウム触媒によるC(sp2)-H結合の不斉ケイ素化を経るスピロシラビフルオレンの合成と反応メカニズムの解明2015

    • Author(s)
      竹内祐太朗、村井征史、髙井和彦
    • Organizer
      第31回若手化学者のための化学道場
    • Place of Presentation
      淡路島
    • Year and Date
      2015-08-27
    • Related Report
      2015 Research-status Report
  • [Presentation] 窒素配位子により安定化されたgem-二亜鉛錯体の単離と構造解析2015

    • Author(s)
      細川直輝、西田悠祐、村井征史、髙井和彦
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Iridium-Catalyzed Intermolecular Dehydrogenative Silylation of Polycyclic Aromatic Compounds without Directing Groups2015

    • Author(s)
      Masahito Murai, Keishi Takami, Kazuhiko Takai
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] ロジウム触媒によるC(sp2)ーH結合の脱水素シリル化反応を利用したシラ[n]ヘリセン誘導体の合成2015

    • Author(s)
      岡田涼、村井征史、髙井和彦
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] ロジウム触媒を用いるC(sp3)ーH結合の脱水素シリル化反応におけるホスフィン配位子の加速効果2015

    • Author(s)
      森田遥香、竹嶋大翔、國信 洋一郎、村井征史、髙井和彦
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] レニウム触媒によるメタントリカルボン酸エステルの1,6-ジインへの逆Markovnikov型付加を経るテトラヒドロインデノン誘導体の合成2015

    • Author(s)
      堀駿介、村井征史、髙井和彦
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] アズレン骨格を有する多環芳香族炭化水素の合成とその物性評価2015

    • Author(s)
      伊場真志、村井征史、髙井和彦
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-26
    • Related Report
      2014 Research-status Report
  • [Presentation] Bismuth(III)-Catalyzed Dehydrative Etherification and Thioetherification of Phenolic Hydroxy Groups2014

    • Author(s)
      Masahito Murai, Kazuki Origuchi, and Kazuhiko Takai
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      福岡
    • Year and Date
      2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] Catalytic anti-Markovnikov Addition of Methanetricarboxylates to Terminal Alkynes via the Rhenium Vinylidene Intermediate2014

    • Author(s)
      Shunsuke Hori, Masahito Murai, and Kazuhiko Takai
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      福岡
    • Year and Date
      2014-09-24
    • Related Report
      2014 Research-status Report
  • [Presentation] Rhenium(VII) Oxide-Catalyzed Stereospecific Deoxygenation of Epoxides to Alkenes Using Phosphites as a Reductant2014

    • Author(s)
      Takuya Nakagiri, Masahito Murai, Kazuhiko Takai
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      福岡
    • Year and Date
      2014-09-24
    • Related Report
      2014 Research-status Report
  • [Presentation] ロジウム触媒を用いるGeーHおよびCーH結合の活性化を経る9-ジベンゾゲルモールの合成2014

    • Author(s)
      松本浩志、岡田涼、村井征史、髙井和彦
    • Organizer
      第31回有機合成化学セミナー
    • Place of Presentation
      福岡
    • Year and Date
      2014-09-17
    • Related Report
      2014 Research-status Report
  • [Presentation] ビスマス触媒によるビニルエーテルからの環形成と芳香族化による多環芳香族化合物の合成2014

    • Author(s)
      細川直輝、前川弘行、村井征史、髙井和彦
    • Organizer
      第31回有機合成化学セミナー
    • Place of Presentation
      福岡
    • Year and Date
      2014-09-17
    • Related Report
      2014 Research-status Report
  • [Presentation] ビスマス触媒による2-(2-アリールフェニル)ビニルエーテルの環化反応を利用したフェナントレン骨格を有する多環芳香族炭化水素の合成2014

    • Author(s)
      村井征史、細川直輝、前川弘行、David Roy、髙井和彦
    • Organizer
      第25回 基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] 多環芳香族化合物へのアズレン骨格の導入とその物性の評価2014

    • Author(s)
      伊場真志、村井征史、髙井和彦
    • Organizer
      第25回 基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07
    • Related Report
      2014 Research-status Report
  • [Presentation] レニウム触媒を用いるb-ケトホスホン酸エステルとアルキンからのオキサホスフォリンオキシドの合成2014

    • Author(s)
      中村誠宏、村井征史、髙井和彦
    • Organizer
      第30回若手化学者のための化学道場
    • Place of Presentation
      岡山
    • Year and Date
      2014-08-29
    • Related Report
      2014 Research-status Report
  • [Presentation] モリブデン触媒による二置換エポキシドの立体選択的な脱酸素反応2014

    • Author(s)
      寒河江貴久、中桐卓也、浅子壮美、村井征史、髙井和彦
    • Organizer
      第30回若手化学者のための化学道場
    • Place of Presentation
      岡山
    • Year and Date
      2014-08-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 遷移金属触媒を用いる多環芳香族炭化水素の効率的合成法とその官能基化法の開発2014

    • Author(s)
      村井征史
    • Organizer
      第3回化学フロンティア研究会
    • Place of Presentation
      岡山
    • Year and Date
      2014-07-26
    • Related Report
      2014 Research-status Report
    • Invited

URL: 

Published: 2014-04-04   Modified: 2018-03-22  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi