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Novel Functions, Properties, and Reactions based on Carborate Anions

Research Project

Project/Area Number 25713001
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypePartial Multi-year Fund
Research Field Chemical pharmacy
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

Takita Ryo  国立研究開発法人理化学研究所, 環境資源科学研究センター, 副チームリーダー (50452321)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥24,050,000 (Direct Cost: ¥18,500,000、Indirect Cost: ¥5,550,000)
Fiscal Year 2015: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2013: ¥13,780,000 (Direct Cost: ¥10,600,000、Indirect Cost: ¥3,180,000)
Keywordsカルボランアニオン / クロスカップリング反応 / 銅 / 共役 / 機能性分子 / クロスカップリング / イオン液晶
Outline of Final Research Achievements

Monocarba-closo-dodecaborate (1; [closo-CB11H12]-, or C1-carborane anion) is a symmetrical and stable anionic cluster, which exhibits σ-aromaticity. In contrast to the rich applications of C2-carboranes (C2B10H12), the chemistry of C1-carborane anion as a platform of functional molecules were not well studied, due to the lack of its efficient functionalization. In particular, no efficient general methods are available for introduction of aryl groups at the carbon vertex of C1-carborane anion.
Thus, we have developed a general and efficient C-C cross-coupling reaction of 1. The use of copper(I) species as a transmetalating partner facilitated the cross-coupling process of the sterically-hindered C1-carborane anion. The potential applications of 1-C-arylated C1-carborane anion derivatives were also explored. Furthermore, conjugation between σ- and π-aromatic moieties in 1-C-arylated C1-carboran anion derivatives has been identified.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (50 results)

All 2016 2015 2014 2013 Other

All Journal Article (13 results) (of which Peer Reviewed: 10 results,  Acknowledgement Compliant: 5 results,  Open Access: 3 results) Presentation (31 results) (of which Int'l Joint Research: 6 results,  Invited: 5 results) Book (1 results) Remarks (5 results)

  • [Journal Article] πおよびσ共役結合に対する新反応開発と機能創出2016

    • Author(s)
      滝田 良
    • Journal Title

      薬学雑誌

      Volume: 136

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Conjugation between σ- and π-Aromaticity in 1-C-Arylated Monocarba-closo-dodecaborate Anions2015

    • Author(s)
      Otsuka, Mai; Takita, Ryo; Kanazawa, Junichiro; Miyamoto, Kazunori; Muranaka, Atsuya; Uchiyama, Masanobu
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 48 Pages: 15082-15085

    • DOI

      10.1021/jacs.5b10321

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Pd-catalyzed Cross-coupling Reaction of Lithiated Monocarba-closo-dodecaborate at the Carbon Vertex2015

    • Author(s)
      Yu Kitazawa, Mai Otsuka, Junichiro Kanazawa, Ryo Takita, and Masanobu Uchiyama
    • Journal Title

      Synlett

      Volume: 26 Issue: 17 Pages: 2403-2407

    • DOI

      10.1055/s-0034-1378833

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Perfluoroalkyl and -aryl Zinc Ate Complexes: Generation, Reactivity, and Synthetic Application2015

    • Author(s)
      Xuan Wang, Keiichi Hirano, Daisuke Kurauchi, Hisano Kato, Naoyuki Toriumi, Ryo Takita, Masanobu Uchiyama
    • Journal Title

      Chemistry-A European Journal

      Volume: 21 Issue: 31 Pages: 10993-10996

    • DOI

      10.1002/chem.201501811

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] The Development of C-C Cross-Coupling Reaction of Monocarba-<i>closo</i>-dodecaborate Anion for the Synthesis of Functional Molecules2014

    • Author(s)
      金澤純一朗、滝田 良、内山真伸
    • Journal Title

      YAKUGAKU ZASSHI

      Volume: 134 Issue: 7 Pages: 783-788

    • DOI

      10.1248/yakushi.14-00017-1

    • NAID

      130004756443

    • ISSN
      0031-6903, 1347-5231
    • Year and Date
      2014-07-01
    • Related Report
      2014 Annual Research Report
    • Open Access
  • [Journal Article] Design, Synthesis, and Structure-activity Relationship Study of Organoantimony Compounds That Induce the Expression of Perlecan in Vascular Endothelial Cells2014

    • Author(s)
      中裕之、滝田 良、鍛冶利幸、内山真伸
    • Journal Title

      YAKUGAKU ZASSHI

      Volume: 134 Issue: 7 Pages: 789-791

    • DOI

      10.1248/yakushi.14-00017-2

    • NAID

      130004756444

    • ISSN
      0031-6903, 1347-5231
    • Year and Date
      2014-07-01
    • Related Report
      2014 Annual Research Report
    • Open Access
  • [Journal Article] Trans-Diborylation of Alkynes: Pseudo-Intramolecular Strategy Utilizing Propargylic Alcohol Unit2014

    • Author(s)
      Y. Nagashima, K. Hirano, R. Takita and M. Uchiyama
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 24 Pages: 8532-8535

    • DOI

      10.1021/ja5036754

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Diastereoselective deprotonative metalation of chiral ferrocene derived acetals and esters using mixed lithiumecadmium and lithiumezinc combinations2014

    • Author(s)
      Gandrath Dayaker, Aare Sreeshailam, D. Venkata Ramana, Floris Chevallier, Thierry Roisnel, Shinsuke Komagawa, Ryo Takita, Masanobu Uchiyama, Palakodety Radha Krishna, and Florence Mongin
    • Journal Title

      Tetrahedron

      Volume: 60 Pages: 2102-2117

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] New avenues in the directed deprotometallation of aromatics: recent advances in directed cupration2014

    • Author(s)
      Philip J. Harford, Andrew J. Peel, Floris Chevallier, Ryo Takita, Florence Mongin, Masanobu Uchiyama, and Andrew E. H. Wheatley
    • Journal Title

      Dalton Transactions

      Volume: 43 Issue: 38 Pages: 14181-14203

    • DOI

      10.1039/c4dt01130a

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Diastereoselective deprotonative metalation of chiral ferrocene derived acetals and esters using mixed lithiumecadmium and lithiumezinc combinations2014

    • Author(s)
      Thierry Roisnel, Shinsuke Komagawa, Ryo Takita, Masanobu Uchiyama, Palakodety Radha Krishna, and Florence Mongin
    • Journal Title

      Tetrahedron

      Volume: 70 Issue: 12 Pages: 2102-2117

    • DOI

      10.1016/j.tet.2014.02.010

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-mediated C-C Cross-Coupling Reaction of Monocarba-closo-dodecaborate Anion for Construction of Functional Molecules2013

    • Author(s)
      Junichiro Kanazawa, Ryo Takita, Aleksandra Jankowiak, Shinya Fujii, Hiroyuki Kagechika, Daisuke Hashizume, Koichi Shudo, Piotr Kaszynski, and Masanobu Uchiyama
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52 Issue: 31 Pages: 8017-8021

    • DOI

      10.1002/anie.201302448

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] [closo-1-CB11H11-1-Ph]- as a Structural Element for Ionic Liquid Crystals2013

    • Author(s)
      Aleksandra Jankowiak, Junichiro Kanazawa, Piotr Kaszynski, Ryo Takita, Masanobu Uchiyama
    • Journal Title

      J. Organomet. Chem.

      Volume: 747 Pages: 195-200

    • DOI

      10.1016/j.jorganchem.2013.05.034

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design, Generation, and Synthetic Application of Borylzincate: Borylation of Aryl Halides and Borylzincation of Benzynes/Terminal Alkyne2013

    • Author(s)
      Yuki Nagashima, Ryo Takita, Kengo Yoshida, Keiichi Hirano, and Masanobu Uchiyama
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 50 Pages: 18730-18733

    • DOI

      10.1021/ja409748m

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] ボレニウム種を活用する触媒的芳香族ホウ素化反応2016

    • Author(s)
      木谷 文也,今堀 龍志,滝田 良,内山 真伸
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 銅試薬の特性を活かした嵩高い化合物を基質とするクロスカップリング反応2016

    • Author(s)
      大井 未来, 大塚 麻衣, 北沢 裕, 金澤 純一朗, 滝田 良, 内山 真伸
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Cross-coupling Reaction of Monocarba-closo-dodecaborate for Innovative Functions2016

    • Author(s)
      滝田 良,大塚 麻衣,大井 未来,北沢 裕,金澤 純一朗,内山真伸
    • Organizer
      CEMS International Symposium on Supramolecular Chemistry and Functional Materials 2016 (CEMSupra 2016)
    • Place of Presentation
      東京大学(東京)
    • Year and Date
      2016-01-13
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Introduction of aromatic rings into C1-carborane anion and their properties2015

    • Author(s)
      大塚麻衣, 金澤純一朗, 滝田 良, 内山真伸
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      ホノルル市(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Copper-mediated cross-coupling reaction: mechanistic insights and its application2015

    • Author(s)
      大井 未来, 大塚 麻衣, 金澤 純一朗, 滝田 良, 内山 真伸
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      ホノルル市(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] “Super activated” lithium cation based on carborane anions and its novel reactivity2015

    • Author(s)
      北沢 裕, 滝田 良 , 松原 誠二郎, 内山 真伸
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      ホノルル市(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Catalytic arene borylation based on in situ-generated borenium species2015

    • Author(s)
      木谷 文也, 今堀 龍志, 滝田 良, 内山 真伸
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      ホノルル市(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Cross-coupling Reaction of Monocarba-closo-dodecaborate for Innovative Functions2015

    • Author(s)
      滝田 良,大塚 麻衣,北沢 裕,金澤 純一朗,内山 真伸
    • Organizer
      The 10th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-10)
    • Place of Presentation
      高雄市(台湾)
    • Year and Date
      2015-11-02
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] C1 カルボランの修飾化反応を基盤とした新物性&#8226;新機能の創出2015

    • Author(s)
      大塚 麻衣,金澤 純一朗,北沢 裕,滝田 良,内山 真伸
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      近畿大学(大阪)
    • Year and Date
      2015-10-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] ボレニウム種を活用する触媒的芳香族ホウ素化反応2015

    • Author(s)
      木谷 文也, 今堀 龍志, 滝田 良, 内山 真伸
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] C1-カルボランアニオンのクロスカップリング反応-反応機構とさらなる展開2015

    • Author(s)
      大井 未来, 大塚 麻衣, 北沢 裕, 金澤 純一朗, 滝田 良, 内山 真伸
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] カルボランアニオンを基盤とする超 Lewis 酸性リチウムカチオンの反応性2015

    • Author(s)
      北沢 裕, 滝田 良, 内山 真伸, 松原 誠二郎
    • Organizer
      第 26 回基礎有機化学討論会
    • Place of Presentation
      愛媛大学(愛媛県松山市)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 元素の特性を活かした反応開発と機能創出2015

    • Author(s)
      滝田 良
    • Organizer
      第一回産総研・理研 触媒化学分野ジョイントワークショップ
    • Place of Presentation
      理化学研究所(埼玉県和光市)
    • Year and Date
      2015-04-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] カルボランアニオンを基盤としたリチウムカチオン超活性化と特異な反応性2015

    • Author(s)
      北沢 裕, 滝田 良 , 松原 誠二郎, 内山 真伸
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉県、日本大学
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] C1-カルボランアニオンへの芳香環導入とその物性2015

    • Author(s)
      大塚 麻衣,金澤 純一朗,滝田 良,内山 真伸
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      兵庫県神戸市、神戸学院大学/兵庫医療大学
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 銅アート錯体を用いた芳香環への位置/化学選択的な水酸基およびアミノ基導入反応の開発2015

    • Author(s)
      下條 弘平,平野 圭一,滝田 良,内山 真伸
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      兵庫県神戸市、神戸学院大学/兵庫医療大学
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 亜鉛錯体の光学特性を利用したタンパク質破壊法の開発2015

    • Author(s)
      佐藤 玄,大井 未来,今堀 龍志,滝田 良,吉田 健吾,石川 稔,橋本 祐一,村中 厚哉,内山 真伸
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      兵庫県神戸市、神戸学院大学/兵庫医療大学
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] πおよびσ共役結合に対する新反応開発と機能創出2015

    • Author(s)
      滝田 良
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      兵庫県神戸市、神戸学院大学/兵庫医療大学
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 元素の特性を活かした新反応開発と機能創出2015

    • Author(s)
      滝田 良
    • Organizer
      千葉大学大学院薬学研究院 第7回化学系若手研究者講演会
    • Place of Presentation
      千葉県、千葉大学
    • Year and Date
      2015-01-23
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ボリルアニオン等価体の設計と新反応開発―ボリル亜鉛アート錯体によるホウ素化反応と擬分子内trans-ジボリル化反応―2014

    • Author(s)
      滝田 良, 永島佑貴, 平野圭一, 内山 真伸
    • Organizer
      第106回有機合成シンポジウム
    • Place of Presentation
      東京都、早稲田大学
    • Year and Date
      2014-11-06 – 2014-11-07
    • Related Report
      2014 Annual Research Report
  • [Presentation] カルボランアニオンのクロスカップリング反応の開発と機能創出2014

    • Author(s)
      滝田 良, 大塚麻衣, 金澤純一朗, 内山 真伸
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      福岡県福岡市、九州大学
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] Cross-coupling Reaction of Monocarba-closo-dodecaborate for Functional Molecules2014

    • Author(s)
      大塚麻衣, 金澤純一朗, 滝田 良, 内山真伸
    • Organizer
      NIMS Conference 2014 &#8211;A Strong Future from Soft Materials&#8211;
    • Place of Presentation
      茨城県つくば市、物質・材料研究機構
    • Year and Date
      2014-07-01 – 2014-07-03
    • Related Report
      2014 Annual Research Report
  • [Presentation] 元素の特性を活かした反応開発と機能性分子創製2014

    • Author(s)
      滝田 良
    • Organizer
      理研シンポジウム:第9回有機合成化学のフロンティア
    • Place of Presentation
      埼玉県和光市 理化学研究所
    • Year and Date
      2014-06-27
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] カルボランアニオンを基盤とする超 Lewis 酸という新概念:リチウムカチオン活性化法と特異な反応性2014

    • Author(s)
      北沢 裕, 滝田 良, 内山 真伸, 松原 誠二郎
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Annual Research Report
  • [Presentation] 銅アート錯体を用いた芳香環への位置選択的・化学選択的な水酸基導入反応の開発2014

    • Author(s)
      下條 弘平, 駒川 晋輔, 滝田 良, 内山 真伸
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      愛知県
    • Related Report
      2013 Annual Research Report
  • [Presentation] 金属錯体中間体を利用したフタロシアニン誘導体の高選択的合成法の開発2014

    • Author(s)
      佐藤 玄,滝田 良, 吉田 健吾, 村中 厚哉, 内山 真伸
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      愛知県
    • Related Report
      2013 Annual Research Report
  • [Presentation] カルボランアニオンによるリチウムカチオン活性化と特異な反応性2013

    • Author(s)
      北沢 裕, 滝田 良, 内山 真伸, 松原誠二郎
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      東京
    • Related Report
      2013 Annual Research Report
  • [Presentation] 銅アート錯体を用いる芳香環 Directed ortho Cuparation の反応機構と直接的水酸基導入反応への応用2013

    • Author(s)
      滝田 良, 下條弘平, 駒川晋輔, 内山 真伸
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Annual Research Report
  • [Presentation] ボリル亜鉛アート錯体を用いたボリル化反応の開発2013

    • Author(s)
      永島 佑貴, 滝田 良, 内山 真伸
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Annual Research Report
  • [Presentation] 元素の特性を活かした反応開発と機能性分子創製

    • Author(s)
      滝田 良
    • Organizer
      平成25年度日本化学会東北支部青森地区講演会
    • Place of Presentation
      青森、弘前大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 元素の特性を活かした反応開発と機能性分子創製

    • Author(s)
      滝田 良
    • Organizer
      平成25年度第1回有機金属若手研究者の会
    • Place of Presentation
      東京、中央大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Book] Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds2015

    • Author(s)
      Floris Chevallier, Florence Mongin, Ryo Takita, and Masanobu Uchiyama
    • Total Pages
      959
    • Publisher
      WILEY
    • Related Report
      2015 Annual Research Report
  • [Remarks] 理化学研究所 環境資源科学研究センター 先進機能元素化学研究チーム/内山元素化学研究室

    • URL

      http://www.riken.jp/genso_kagaku/index.html

    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
  • [Remarks] 東京大学大学院薬学系研究科 基礎有機化学教室

    • URL

      http://www.f.u-tokyo.ac.jp/~kisoyuki/

    • Related Report
      2015 Annual Research Report
  • [Remarks] 東京大学大学院薬学系研究科 基礎有機化学教室

    • URL

      http://www.f.u-tokyo.ac.jp/~kisoyuki/index.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 東京大学大学院薬学系研究科 基礎有機化学教室

    • URL

      http://www.f.u-tokyo.ac.jp/~kisoyuki/

    • Related Report
      2013 Annual Research Report
  • [Remarks] 理化学研究所 環境資源科学研究センター 先進機能元素化学研究チーム

    • URL

      http://www.riken.jp/genso_kagaku/index.html

    • Related Report
      2013 Annual Research Report

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Published: 2013-05-21   Modified: 2019-07-29  

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