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Development of Practical Synthetic Methods Using Palladium-Catalyzed C-H Functionalization

Research Project

Project/Area Number 20790004
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

KIYOFUMI Inamoto  Tohoku University, 大学院・薬学研究科, 助教 (30359533)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsパラジウム / 炭素-水素結合官能基化 / 炭素-窒素結合形成反応 / 炭素-硫黄結合形成反応 / 複素環化合物 / 2-キノリノン / ベンゾチアゾール / 再酸化剤 / 炭素-水素結合活性化 / インドール / ベンゾチオフェン
Research Abstract

Catalytic methods for the synthesis of heterocyclic compounds, such as indazoles, indoles, 2-quinolinones, benzo[b]thiophenes, and benzothiazoles, were developed utilizing palladium-catalyzed C-H functionalization followed by intramolecular C-N or C-S bond formation. These heterocyclic compounds are subunits of a range of biologically active pharmaceuticals and natural products.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (32 results)

All 2010 2009 2008 Other

All Journal Article (12 results) (of which Peer Reviewed: 11 results) Presentation (18 results) Remarks (2 results)

  • [Journal Article] Functionalization of Carbon-Hydrogen Bond by Palladium Catalyst. Ring Construction in Indazole, Indole, Benzothiophene, and Benzothiazole Synthesis2010

    • Author(s)
      Kiyofumi Inamoto
    • Journal Title

      Farumashia 46(3)

      Pages: 229-234

    • Related Report
      2009 Final Research Report
  • [Journal Article] Pincer-Type Bis(carbene)-Derived Complexes of Nickel(II) : Synthesis, Structure, and Catalytic Activity2009

    • Author(s)
      Kiyofumi Inamoto, Jun-ichi Kuroda, Eunsang Kwon, Kou Hiroya, Takayuki Doi
    • Journal Title

      Journal of Organometallic Chemistry 694(3)

      Pages: 389-396

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] N-Heterocyclic Carbene-Derived Nickel-Pincer-Complexes : Efficient and Applicable Catalysts for Suzuki-Miyaura Coupling Reactions of Aryl/Alkenyl Tosylates and Mesylates2009

    • Author(s)
      Jun-ichi Kuroda, Kiyofumi Inamoto, Kou Hiroya, Takayuki Doi
    • Journal Title

      European Journal of Organic Chemistry 10

      Pages: 2251-2261

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 6Z-Pandanamine by Regioselective Cyclization Reaction of 2-En-4-ynoic Acid Derivatives Promoted by Weak Base2009

    • Author(s)
      Kou Hiroya, Kazuya Takuma, Kiyofumi Inamoto, Takao Sakamoto
    • Journal Title

      Heterocycles 77(1)

      Pages: 493-505

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the Core Ring System of Awajanomycin from N-Boc-3-methoxycarbonyl-2-pyridinone2009

    • Author(s)
      Kou Hiroya, Kei Kawamoto, Kiyofumi Inamoto, Takao Sakamoto, Takayuki Doi
    • Journal Title

      Tetrahedron Letters 50(18)

      Pages: 2115-2118

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Diastereoselective Birch Reduction-Alkylation Reactions of Bi-and Tricyclic β-Alkoxy-α, β-unsaturated Ketones2009

    • Author(s)
      Kou Hiroya, Yusuke Ichihashi, Ai Furutono, Kiyofumi Inamoto, Takao Sakamoto, Takayuki Doi
    • Journal Title

      Journal of Organic Chemistry 74(17)

      Pages: 6623-6630

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Synthesis of 2-Substituted Benzothiazoles via a C-H Functionalization/Intramolecular C-S Bond Formation Process2008

    • Author(s)
      Kiyofumi Inamoto, Chisa Hasegawa, Kou Hiroya, Takayuki Doi
    • Journal Title

      Organic Letters 10(22)

      Pages: 5147-5150

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalysed Direct Synthesis of Benzo[b]thiophenes from Thioenols2008

    • Author(s)
      Kiyofumi Inamoto, Yukari Arai, Kou Hiroya, Takayuki Doi
    • Journal Title

      Chemical Communications 43

      Pages: 5529-5531

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] A New Approach to 3-Substituted Indoles through Pd-Catalyzed C-H Activation Followed by Intramolecular Amination Reaction of Enamines2008

    • Author(s)
      Kiyofumi Inamoto, Tadataka Saito, Kou Hiroya, Takayuki Doi
    • Journal Title

      Synlett 20

      Pages: 3157-3162

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalysed Direct Synthesis of Benzo[b]thiophenes from Thioenols2008

    • Author(s)
      Kiyofumi Inamoto, Yukari Arai, Kou Hiroya, Takayuki Doi
    • Journal Title

      Chemical Communications

      Pages: 5529-5531

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Synthesis of 2-Substituted Benzothiazoles via a C-H Functionalization/Intramolecular C-S BoiYd Formation Process2008

    • Author(s)
      Kiyofumi Inamoto, Chisa Hasegawa, Kou Hiroya, Takayuki Doi
    • Journal Title

      Organic Letters 10

      Pages: 5147-5150

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A New Approach to 3-Substituted Indoles through Palladium-Catalyzed C-H Activation Followed by Intramolecular Amination Reaction of Enamines2008

    • Author(s)
      Kiyofumi Inamoto, Tadataka Saito Kou Hiroya, Takayuki Doi
    • Journal Title

      Synlett

      Pages: 3157-3162

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] 酸素を再酸化剤として利用するパラジウム触媒を用いたC-H官能基化によるベンゾチアゾール合成2010

    • Author(s)
      稲本浄文, 長谷川千紗, 川崎順平, 廣谷功, 土井隆行
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] パラジウム触媒による炭素-水素結合官能基化を利用した効率的含窒素複素環化合物の合成研究2009

    • Author(s)
      稲本浄文, 齋藤孔隆, 廣谷功, 土井隆行
    • Organizer
      第24回有機合成化学若手研究者の仙台セミナー
    • Place of Presentation
      仙台
    • Year and Date
      2009-11-28
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] パラジウム触媒による分子内炭素-水素結合官能基化を利用した新規ベンゾチアゾール環構築法の開発2009

    • Author(s)
      稲本浄文, 長谷川千紗, 川崎順平, 廣谷功, 土井隆行
    • Organizer
      第96回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2009-11-06
    • Related Report
      2009 Annual Research Report
  • [Presentation] パラジウム触媒によるC-Hアミノ化反応を利用した4-アリール-2-キノロン類合成2009

    • Author(s)
      稲本浄文, 齋藤孔隆, 廣谷功, 土井隆行
    • Organizer
      第48回日本薬学会東北支部大会
    • Place of Presentation
      仙台
    • Year and Date
      2009-10-18
    • Related Report
      2009 Annual Research Report
  • [Presentation] パラジウム触媒による炭素-水素結合活性化と続く分子内アミノ化反応を利用した効率的2-キノロン誘導体合成法の開発2009

    • Author(s)
      稲本浄文, 齋藤孔隆, 廣谷功, 土井隆行
    • Organizer
      第39回複素環化学討論会
    • Place of Presentation
      柏
    • Year and Date
      2009-10-15
    • Related Report
      2009 Annual Research Report
  • [Presentation] Palladium-Catalyzed C-H Functionalization for the Synthesis of Heterocyclic Compounds2009

    • Author(s)
      稲本浄文, 齋藤孔隆, 長谷川千紗, 川崎順平, 廣谷功, 土井隆行
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis of Nitrogen-Based Heterocyclic Compounds via Palladium-Catalyzed C-H Functionalization2009

    • Author(s)
      稲本浄文, 齋藤孔隆, 長谷川千紗, 廣谷功, 土井隆行
    • Organizer
      15^<th> IUPAC International Symposium on Organometallic Chemistry Directed towards Organic Synthesis
    • Place of Presentation
      グラスゴー, イギリス
    • Year and Date
      2009-07-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] パラジウム触媒による炭素-水素結合活性化と続く分子内炭素-硫黄結合形成反応を利用する新規ベンゾチアゾール環構築法の開発2009

    • Author(s)
      稲本浄文, 長谷川千紗, 廣谷功, 土井隆行
    • Organizer
      第6回東北大学バイオサイエンスシンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2009-06-16
    • Related Report
      2009 Annual Research Report
  • [Presentation] パラジウム触媒による炭素-水素結合官能基化を利用した効率的複素環化合物構築法の開発2009

    • Author(s)
      稲本浄文, 齋藤孔隆, 長谷川千紗, 廣谷功, 土井隆行
    • Organizer
      第95回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2009-06-10
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] パラジウム触媒による炭素-水素結合活性化と続く分子内炭素-硫黄結合形成反応を利用する, 新規ベンゾチアゾール環構築法の開発2009

    • Author(s)
      稲本浄文, 長谷川千紗, 廣谷功, 土井隆行
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒による炭素-水素結合活性化を利用した効率的含窒素複素環化合物構築法の開発2009

    • Author(s)
      稲本浄文, 齋藤孔隆, 廣谷功, 土井隆行
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒による炭素-水素結合活性化を利用した効率的含硫黄複素環化合物構築法の開発2008

    • Author(s)
      稲本浄文, 荒井ゆかり, 長谷川千紗, 廣谷功, 土井隆行
    • Organizer
      第27回メディシナルケミストリーシンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2008-11-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒炭素-水素結合活性化を利用する新規置換インドール類合成法の開発2008

    • Author(s)
      稲本浄文, 齋藤孔隆, 廣谷功, 土井隆行
    • Organizer
      第38回複素環化学討論会
    • Place of Presentation
      広島
    • Year and Date
      2008-11-22
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒炭素-水素結合活性化を利用する効率的含硫黄複素環化合物構築法の開発2008

    • Author(s)
      稲本浄文, 荒井ゆかり, 長谷川千紗, 廣谷功, 土井隆行
    • Organizer
      第38回複素環化学討論会
    • Place of Presentation
      広島
    • Year and Date
      2008-11-21
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] パラジウム触媒を用いたチオエノール類からの直接的ベンゾチオフェン化合物合成法の開発2008

    • Author(s)
      稲本浄文, 荒井ゆかり, 廣谷功, 土井隆行
    • Organizer
      第47回日本薬学会東北支部大会
    • Place of Presentation
      岩手
    • Year and Date
      2008-10-16
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒炭素-水素結合活性化と続く分子内炭素-硫黄結合形成反応を利用する, 新規ベンゾチアゾール環構築法の開発2008

    • Author(s)
      稲本浄文, 長谷川千紗, 廣谷功, 土井隆行
    • Organizer
      第47回日本薬学会東北支部大会
    • Place of Presentation
      岩手
    • Year and Date
      2008-10-16
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒閉環反応を利用する新規ベンゾチオフェン環構築法の開発2008

    • Author(s)
      稲本浄文, 荒井ゆかり, 廣谷功, 土井隆行
    • Organizer
      平成20年度化学系学協会東北大会
    • Place of Presentation
      青森
    • Year and Date
      2008-10-13
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] Synthesis of Indoles and Benzothiophenes via Palladium-Catalyzed C-H Activation. (P-28)2008

    • Author(s)
      Kiyofumi Inamoto, Yukari Arai, Tadataka Saito, Kou Hiroya, Takayuki Doi
    • Organizer
      The 12th Japan-Korea Joint Symposium on Drug Design and Development
    • Place of Presentation
      仙台
    • Year and Date
      2008-05-15
    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/index.html

    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/index.html

    • Related Report
      2009 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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