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

Development of Ubiquitous Metal-Catalyzed Novel Reactions and TheirApplication to the Synthesis of π-Conjugated Molecules

Research Project

Project/Area Number 23750100
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

ILIES Laurean  東京大学, 大学院・理学系研究科, 助教 (40569951)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords鉄触媒 / 銅触媒 / フェナントレン誘導体 / インデン誘導体 / 芳香族スルフォン酸クロリド / 合成化学 / 炭素-水素結合活性化 / 多環芳香族化合物
Research Abstract

We have developed several new synthetic methods that use ubiquitous, inexpensive, and non-toxic metals such as iron, cobalt, copper as the catalyst, and we exploited these methods for the synthesis of π-conjugated materials of interest for materials science. For example, we developed an iron-catalyzed C-H activation reaction for the synthesis of polysubstituted phenanthrenes, naphthalenes, and congeners, compounds of interest as p-type organic semiconductors. A related reactivity of cobalt was exploited for the alkylation of C-H bonds with alkyl chlorides or alkenes, of interest for the late-stage solubilization of π-conjugated materials or for morphology control in liquid crystals. We also exploited inexpensive, commercially available aromatic sulfonyl chlorides as chlorosulfonylation and arylation reagents in the presence of a copper catalyst to synthesize polysubstituted olefins and indene derivatives, some of them showing strong fluorescence in solution and solid state.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (51 results)

All 2013 2012 2011 Other

All Journal Article (17 results) (of which Peer Reviewed: 17 results) Presentation (32 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Iron-Catalyzed Allylic Arylation of Olefins via C(sp3)-H Activation under Mild Conditions2013

    • Author(s)
      M. Sekine, L. Ilies, E. Nakamura
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 3 Pages: 714-717

    • DOI

      10.1021/ol400056z

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Chemo- and Stereoselective Hydromagnesiation of Diarylalkynes and Diynes2012

    • Author(s)
      L. Ilies, T. Yoshida, E. Nakamura
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 41 Pages: 16951-16954

    • DOI

      10.1021/ja307631v

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Polysubstituted Naphthalenes by Iron-Catalyzed [2+2+2] Annulation of Grignard Reagents with Alkynes2012

    • Author(s)
      L. Ilies, A. Matsumoto, M. Kobayashi, N. Yoshikai, E. Nakamura
    • Journal Title

      Synlett

      Volume: 23 Issue: 16 Pages: 2381-2384

    • DOI

      10.1055/s-0032-1317077

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-catalyzed regio- and stereoselective chlorosulfonylation of terminal alkynes with aromatic sulfonyl chlorides2012

    • Author(s)
      X. Zeng
    • Journal Title

      Org. Lett., 14

      Volume: 14 Issue: 3 Pages: 954-956

    • DOI

      10.1021/ol203446t

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand2012

    • Author(s)
      Y. Nakamura
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 13 Pages: 3136-3319

    • DOI

      10.1021/ol301195x

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed ortho Monoarylation of Benzamide Derivatives2012

    • Author(s)
      L. Ilies, E. Konno, Q. Chen, E. Nakamura
    • Journal Title

      Asian J. Org. Chem.,

      Volume: 1 Issue: 2 Pages: 142-145

    • DOI

      10.1002/ajoc.201200042

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Synthesis of Diarylamines via Oxidatively Induced C-N Bond Formation at Room Temperature2012

    • Author(s)
      L. Ilies, T. Matsubara, E. Nakamura
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 21 Pages: 5570-5573

    • DOI

      10.1021/ol302688u

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 鉄を触媒とする不活性炭素-水素結合の直接官能基化2012

    • Author(s)
      Laurean Ilies
    • Journal Title

      月刊ファインケミカル

      Volume: 41 Pages: 40-45

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Nitrogen-Directed Coupling of Arene and Aryl Bromides Mediated by Metallic Magnesium2012

    • Author(s)
      Laurean Ilies, Kotoaki Kobayashi, Arimasa Matsumoto, Naohiko Yoshikai, Eiichi Nakamura
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 354 Issue: 4 Pages: 593-596

    • DOI

      10.1002/adsc.201100791

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Functionalized 1H-Indenes via Copper-Catalyzed Arylative Cyclization of Arylalkynes with Aromatic Sulfonyl Chlorides2011

    • Author(s)
      Xiaoming Zeng, Laurean Ilies, 中村栄一
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 44 Pages: 17638-17640

    • DOI

      10.1021/ja209300c

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] on-Catalyzed Stereospecific Activation of Olefinic C-H Bonds with Grignard Reagent for Synthesis of Substituted Olefi2011

    • Author(s)
      イリエシュラウレアン, 浅子壮美, 中村栄一
    • Journal Title

      Journal of the Amrican Chemical Society

      Volume: 133 Issue: 20 Pages: 7672-7675

    • DOI

      10.1021/ja2017202

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Phenanthrene Synthesis by Iron-Catalyzed [4 + 2] Benzannulation between Alkyne and Biaryl or 2-Alkenylphenyl Grignard Reagent2011

    • Author(s)
      A. Matsumoto
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 133 Issue: 17 Pages: 6557-6559

    • DOI

      10.1021/ja201931e

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cobalt-catalyzed coupling of alkyl Grignard reagent with benzamide and 2-phenylpyridine derivatives through directed C-H bond activation under air,2011

    • Author(s)
      Q. Chen
    • Journal Title

      Org. Lett.

      Volume: 13 Issue: 12 Pages: 3232-3234

    • DOI

      10.1021/ol2011264

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed Chemoselective Insertion of Alkene into the Ortho C-H Bond of Benzamide2011

    • Author(s)
      Laurean Ilies, Quan Chen, Xiaoming Zeng, Eiichi Nakamura
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Issue: 14 Pages: 5221-5223

    • DOI

      10.1021/ja200645w

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed ortho-Alkylation of Secondary Benzamide with Alkyl Chloride through Directed C-H Bond Activation2011

    • Author(s)
      Quan Chen, Laurean Ilies, Eiichi Nakamura
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Issue: 3 Pages: 428-429

    • DOI

      10.1021/ja1099853

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Oxidative Monoarylation of Primary Amines with Organozinc Reagents2011

    • Author(s)
      Y.Nakamura, L.Ilies, E.Nakamura
    • Journal Title

      Organic Letters

      Volume: 13 Issue: 22 Pages: 5998-6001

    • DOI

      10.1021/ol2024357

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed C-H Bond Activation for the ortho-Arylation of Aryl Pyridines and Imines with Grignard Reagents2011

    • Author(s)
      吉戒直彦, 浅子壮美, 山川健司, イリエシュラウレアン, 中村栄一
    • Journal Title

      Chemistry-An Asian Journal

      Volume: 6 Issue: 11 Pages: 3059-3065

    • DOI

      10.1002/asia.201100470

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 鉄触媒を用いた有機亜鉛試薬による sp3 炭素-水素結合の直接 アリール化反応2013

    • Author(s)
      尚睿
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学,びわこ・くさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒を用いたアリルフェニルエーテルによる芳香族炭素-水素結合の直接アリル化反応2013

    • Author(s)
      浅子壮美
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学,びわこ・くさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒を用いた1,3-ジイン類に対する選択的カルボマグネシウム化による1,3-エンイン類の合成2013

    • Author(s)
      吉田拓未
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学,びわこ・くさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] Nakamura, "Cobalt-Catalyzed ortho-Alkylation of Benzamides via C-H Bond Activation2012

    • Author(s)
      Laurean Ilies, Quan Chen, Xiaoming Zeng, Eiichi
    • Organizer
      25^th International Conference on Organometallic Chemistry (ICOMC 2012)
    • Place of Presentation
      Lisbon, Portugal
    • Year and Date
      2012-09-06
    • Related Report
      2012 Final Research Report
  • [Presentation] Iron- or Nickel-Catalyzed Oxidatively-Induced C-N Bond Formation2012

    • Author(s)
      Laurean Ilies, Yuki Nakamura, Tatsuaki Matsubara, Eiichi Nakamura
    • Organizer
      25^th International Conference on Organometallic Chemistry (ICOMC 2012)
    • Place of Presentation
      Lisbon, Portugal
    • Year and Date
      2012-09-03
    • Related Report
      2012 Final Research Report
  • [Presentation] Cobalt-Catalyzed C-H Activation for ortho-Alkylation of Benzamides2012

    • Author(s)
      Laurean Ilies, Quan Chen, Xiaoming Zeng, Eiichi Nakamura
    • Organizer
      Gordon Research Conference on Organometallic Chemistry
    • Place of Presentation
      Salve Regina University, USA
    • Related Report
      2012 Final Research Report
  • [Presentation] Cobalt-Catalyzed C-H Activation for ortho-Alkylation of Benzamides2012

    • Author(s)
      Laurean Ilies
    • Organizer
      Gordon Research Conference on Organometallic Chemistry
    • Place of Presentation
      Salve Regina University, Newport, USA
    • Related Report
      2012 Annual Research Report
  • [Presentation] Iron- or Nickel-Catalyzed Oxidatively-Induced C-N Bond Formation2012

    • Author(s)
      Laurean Ilies
    • Organizer
      25th International Conference on Organometallic Chemistry
    • Place of Presentation
      Lisbon, Portugal
    • Related Report
      2012 Annual Research Report
  • [Presentation] Cobalt-Catalyzed ortho-Alkylation of Benzamides via C-H Bond Activation2012

    • Author(s)
      Laurean Ilies
    • Organizer
      25th International Conference on Organometallic Chemistry
    • Place of Presentation
      Lisbon, Portugal
    • Related Report
      2012 Annual Research Report
  • [Presentation] ニッケル触媒による酸化的炭素-窒素結合形成反応2012

    • Author(s)
      松原立明
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒によるアリル位C-H結合の位置選択的モノアリール化反応2012

    • Author(s)
      関根真樹
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒を用いたジアリールアルキン及びジイン類の選択的ヒドロマグネシウム化反応2012

    • Author(s)
      吉田拓未
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] ニッケル触媒を用いた室温下における酸化的炭素-窒素結合形成反応2012

    • Author(s)
      松原立明
    • Organizer
      第2回CSJ化学フェスタ
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒を用いたジアリールアルキン及びジイン類の立体及び化学選択的ヒドロマグネシウム化反応2012

    • Author(s)
      吉田拓未
    • Organizer
      第2回CSJ化学フェスタ
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] ニッケル触媒を用いたポリフルオロアレーンの選択的モノ置換反応における配位子効果のDFT法による検討2012

    • Author(s)
      浅子壮美
    • Organizer
      第2回CSJ化学フェスタ
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] First-Row Transition Metal-Catalyzed C-H Bond Functionalization2011

    • Author(s)
      イリエシュラウレアン
    • Organizer
      第八回 有機元素化学セミ ナー
    • Place of Presentation
      京都大学,宇治
    • Year and Date
      2011-11-22
    • Related Report
      2012 Final Research Report
  • [Presentation] Iron- and Cobalt-Catalyzed Regioselective Aromatic and Olefinic C-H Bond Functionalization2011

    • Author(s)
      Laurean Ilies, Quan Chen, Sobi Asako, Xiaoming Zeng, and Eiichi Nakamura
    • Organizer
      The 16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS), P-249
    • Place of Presentation
      Shanghai,China
    • Related Report
      2012 Final Research Report
  • [Presentation] 銅触媒を用いた芳香族スルホン酸クロリドとアリールアルキンとの環化反応による多置換インデン誘導体の合成

    • Author(s)
      Xiaoming Zeng・イリエシュ ラウレアン・中村 栄一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学 神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] ニッケル触媒を用いた炭素―フッ素結合活性化を経るポリフルオロアレーンの選択的モノ置換反応

    • Author(s)
      中村 優希・浅子壮美・吉戒直彦・イリエシュ ラウレアン・中村 栄一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学 神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒を用いたヒドロメタル化によるアルケニルマグネシウムの合成とその応用

    • Author(s)
      吉田拓未・イリエシュ ラウレアン・中村 栄一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学 神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] 室温下におけるニッケル触媒を用いたグリニャール試薬による第一級アミン化合物の酸化的モノアリール化反応

    • Author(s)
      松原立明,中村 優希・イリエシュ ラウレアン・中村 栄一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学 神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒を用いたラジカル生成反応を経る脂肪族炭素ー水素結合のアリール化反応

    • Author(s)
      関根真樹・イリエシュ ラウレアン・中村栄一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学 神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒を用いたアルキンとグリニャール試薬の[2 + 2 + 2]環化反応による多環芳香族化合物の合成

    • Author(s)
      小林幹明・松本有正・イリエシュ ラウレアン・吉戒直彦・中村栄一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学 神奈川
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒による炭素-水素結合活性化を用いたアルキンとビアリールグリニャール試薬の環化反応

    • Author(s)
      松本有正・イリエシュ ラウレアン・中村栄一
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学
    • Related Report
      2011 Research-status Report
  • [Presentation] First-Row Transition Metal-Catalyzed C-H Bond Functionalization

    • Author(s)
      イリエシュ ラウレアン
    • Organizer
      第八回 有機元素化学セミナー(招待講演)
    • Place of Presentation
      京都大学 宇治
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒とグリニャール試薬を用いた立体特異的 オレフィン炭素-水素結合活性化による置換オレフィ ン合成

    • Author(s)
      浅子壮美・イリエシュ ラウレアン・中村栄一
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒による亜鉛アミドと有機亜鉛試薬の酸化的カップリング反応を用いたジアリールアミンの合成

    • Author(s)
      中村 優希・イリエシュ ラウレアン・中村 栄一
    • Organizer
      日本化学会第5回関東支部大会
    • Place of Presentation
      東京農工大学
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒と有機亜鉛試薬による炭素-水素結合活性化を経るベンズアミド誘導体のアリール化反応

    • Author(s)
      金野栄太・陳全・イリエシュ ラウレアン・中村栄一
    • Organizer
      第5回関東支部大会
    • Place of Presentation
      東京農工大学
    • Related Report
      2011 Research-status Report
  • [Presentation] Iron-Catalyzed Oxidative C-N Bond Formation using Zinc Amide and Organozinc Reagent

    • Author(s)
      中村 優希・イリエシュ ラウレアン・中村 栄一
    • Organizer
      The 16th IUPAC International Symposiumon Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS)
    • Place of Presentation
      Shanghai, China
    • Related Report
      2011 Research-status Report
  • [Presentation] Insertion of 1- and 2-Alkene into the Ortho C-H Bond of Benzamide through Cobalt-Catalyzed C-H Bond Activation

    • Author(s)
      Quan Chen・Xiaoming Zeng・イリエシュ ラウレアン・中村 栄一
    • Organizer
      The 16th IUPAC International Symposiumon Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS)
    • Place of Presentation
      Shanghai, China
    • Related Report
      2011 Research-status Report
  • [Presentation] Phenanthrene Synthesis via Iron-Catalyzed Annulation of Alkyne with Grignard Reagent

    • Author(s)
      松本有正・イリエシュ ラウレアン・中村栄一
    • Organizer
      The 16th IUPAC International Symposiumon Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS)
    • Place of Presentation
      Shanghai, China
    • Related Report
      2011 Research-status Report
  • [Presentation] Iron- and Cobalt-Catalyzed Regioselective Aromatic and Olefinic C-H Bond Functionalization

    • Author(s)
      イリエシュ ラウレアン・Quan Chen・浅子壮美・ Xiaoming Zeng・中村 栄一
    • Organizer
      The 16th IUPAC International Symposiumon Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS)
    • Place of Presentation
      Shanghai, China
    • Related Report
      2011 Research-status Report
  • [Book] 鉄を触媒とする不活性炭素-水素結合の直接官能基化2012

    • Author(s)
      イリエシュ ラウレアン・中村栄一,ファインケミカル
    • Publisher
      鉄触媒の最新研究動向
    • Related Report
      2012 Final Research Report
  • [Remarks] 有機合成・物理有機化学 東京大学大学院理学系研究科化学専攻 中村研究室

    • URL

      http://www.chem.s.u-tokyo.ac.jp/users/common/NakamuraLab.html

    • Related Report
      2012 Annual Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi