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Development of Synthetic Methods for HeterocyclesUsing Palladium-Catalyzed C-H Functionalization

Research Project

Project/Area Number 23790002
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionTohoku University

Principal Investigator

INAMOTO Kiyofumi  東北大学, 大学院・薬学研究科, 助教 (30359533)

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: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords触媒・化学プロセス / 有機化学 / パラジウム / C-H官能基化 / 複素環化合物 / C-H官能基化 / C-H 官能基化
Research Abstract

A novel catalytic method for synthesizing 4-aryl-2-quinolinones was developed that involves two mechanistically independent, sequential palladium-catalyzed reactions-the oxidative Heck reaction and the intramolecular C-H amidation-both of which smoothly proceeded in the presence of a single, palladium-based catalytic system. In addition, it was found that water can be successfully employed as a reaction medium in palladium-catalyzed C-H cyclization of thiobenzanilides. Reactions efficiently proceeded under considerably mild conditions in water, providing a more practical, greener method for the synthesis of 2-arylbenzothiazoles.

Report

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

    (34 results)

All 2013 2012 2011 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (21 results) (of which Invited: 2 results) Book (2 results) Remarks (2 results)

  • [Journal Article] Palladium-catalyzed C-H cyclization in water: a milder route to2-arylbenzothiazoles2012

    • Author(s)
      Kiyofumi Inamoto, Kanako Nozawa, Yoshinori Kondo
    • Journal Title

      Synlett

      Volume: 23 Issue: 11 Pages: 1678-1682

    • DOI

      10.1055/s-0031-1291164

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Tandem-type Pd(II)-catalyzed oxidative Heck reaction/intramolecular C-H amidation sequence : a novel route to 4-aryl-2-quinolinones2012

    • Author(s)
      Kiyofumi Inamoto, Junpei Kawasaki, Kou Hiroya, Yoshinori Kondo, Takayuki Doi
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 36 Pages: 4332-4334

    • DOI

      10.1039/c2cc30600j

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Highly Sensitive Fluorescence Method Reveals the Presence of Palladium in a Cross-Coupling Reaction Mixture Not Treated with Transition Metals2012

    • Author(s)
      Kiyofumi Inamoto, Laura D. Campbell, Takayuki Doi, Kazunori Koide
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Issue: 25 Pages: 3147-3148

    • DOI

      10.1016/j.tetlet.2012.04.043

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 3-carboxylated indoles through a tandem process involving cyclization of 2-ethynylanilines followed by CO2 fixation in the absence of transition metal catalysists2012

    • Author(s)
      K. Inamoto, N. Asano, Y. Nakamura, M. Yonemoto, Y. Kondo
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 10 Pages: 2622-2625

    • DOI

      10.1021/ol300958c

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient useof a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water2012

    • Author(s)
      Kiyofumi Inamoto, Kanako Nozawa, JunKadokawa, Yoshinori Kondo
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 38 Pages: 7794-7798

    • DOI

      10.1016/j.tet.2012.07.042

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic deprotonative functionalization of C(sp2)-H and C(sp3)-H bonds using in situ generated onium amide2012

    • Author(s)
      K. Inamoto, H. Okawa, H. Taneda, M. Sato, Y. Hirono, M. Yonemoto, Y. Kondo
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 78 Pages: 9771-9773

    • DOI

      10.1039/c2cc35701a

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A copper-based catalytic system for carboxylation of terminal alkynes: synthesis of alkyl 2-alkynoates2012

    • Author(s)
      K. Inamoto, N. Asano, K. Kobayashi, M. Yonemoto, Y. Kondo
    • Journal Title

      Organic & Biomelecular Chemistry

      Volume: 10 Issue: 8 Pages: 1514-1516

    • DOI

      10.1039/c2ob06884b

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Use of Dimethyl Carbonate as a Solvent Greatly Enhances the Biaryl Coupling of Aryl Iodides and Organoboron Reagents without Adding Any Transition Metal Catalysts2012

    • Author(s)
      K.Inamoto, C.Hasegawa, K.Hiroya, Y.Kondo, T.Osako, Y.Uozumi, T.Doi
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 23 Pages: 2912-2914

    • DOI

      10.1039/c2cc17401d

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Micellar system in copper-catalyzed hydroxylation of arylboronic acids : facile access to phenols2011

    • Author(s)
      K.Inamoto, K.Nozawa, M.Yonemoto, Y.Kondo
    • Journal Title

      Chemical Communications

      Volume: 47 Issue: 42 Pages: 11775-11777

    • DOI

      10.1039/c1cc14974a

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 遷移金属触媒および有機分子触媒を駆使する不活性炭素-水素結合修飾反応:触媒的高度分子変換プロセスの開発2013

    • Author(s)
      稲本浄文
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜(招待講演)
    • Year and Date
      2013-03-29
    • Related Report
      2012 Final Research Report
  • [Presentation] 遷移金属触媒および有機分子触媒を駆使する不活性炭素-水素結合修飾反応:触媒的高度分子変換プロセスの開発2013

    • Author(s)
      稲本 浄文
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] ルテニウム触媒 C-H カルボニル化反応を用いたクマリン類の新規合成法の開発2013

    • Author(s)
      門川 純
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] 種田 宏2013

    • Author(s)
      オニウムアミド塩基を用いた C(sp3)-H 脱プロトン化-修飾反応の開発
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] パラジウム触媒C-Hアミノ化を基盤とする新規2-キノリノン類合成法の開発2012

    • Author(s)
      稲本浄文,川崎順平,齋藤孔隆,廣谷功,土井隆行,根東義則
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Year and Date
      2012-10-12
    • Related Report
      2012 Final Research Report
  • [Presentation] パラジウム触媒 C-H アミノ化を基盤とする新規 2-キノリノン類合成法の開発2012

    • Author(s)
      稲本 浄文
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] 有機触媒によるアミノシランの活性化を介した芳香複素環化合物の修飾反応2012

    • Author(s)
      大川 ひとみ
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] 界面活性剤を用いた水中での銅触媒 N-アリール化反応2012

    • Author(s)
      門川 純
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] オニウムアミド塩基による触媒的脱プロトン化-修飾反応の開発2012

    • Author(s)
      稲本 浄文
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis of 2-Substituted Benzothiazoles via Palladium-Catalyzed C-H Functionalization/C-S Bond Formation2011

    • Author(s)
      稲本浄文,長谷川千紗,川崎順平,廣谷功,土井隆行,根東義則
    • Organizer
      OMCOS 16
    • Place of Presentation
      上海,中国
    • Year and Date
      2011-07-25
    • Related Report
      2012 Final Research Report
  • [Presentation] パラジウム触媒による C-H 結合官能基化を基盤とする新規複素環構築手法の開発

    • Author(s)
      稲本 浄文
    • Organizer
      第101回有機合成シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Annual Research Report
  • [Presentation] パラジウムを用いた触媒的炭素―水素結合官能基化を基盤とする新規分子変換プロセスの開拓

    • Author(s)
      稲本 浄文
    • Organizer
      日本薬学会東北支部学術講演会
    • Place of Presentation
      仙台
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] フッ化オニウムによるアミノシランの活性化を介した芳香複素環の修飾反応

    • Author(s)
      大川 ひとみ
    • Organizer
      第51回日本薬学会東北支部大会
    • Place of Presentation
      青森
    • Related Report
      2012 Annual Research Report
  • [Presentation] 界面活性剤を用いた銅触媒による N-アリール化反応

    • Author(s)
      門川 純
    • Organizer
      フルオラス科学研究会第5回シンポジウム
    • Place of Presentation
      仙台
    • Related Report
      2012 Annual Research Report
  • [Presentation] パラジウム触媒C-H官能基化による2位置換ベンゾチアゾール合成

    • Author(s)
      稲本 浄文
    • Organizer
      The 16th IUPAC International Symposium OMCOS 16
    • Place of Presentation
      上海,中国
    • Related Report
      2011 Research-status Report
  • [Presentation] C-H官能基化~C-S結合形成によるチオベンズアニリドからのベンゾチアゾール環構築

    • Author(s)
      稲本 浄文
    • Organizer
      第22回メディシナル及び精密化学に関する日仏シンポジウム
    • Place of Presentation
      ルーアン,フランス
    • Related Report
      2011 Research-status Report
  • [Presentation] 界面活性剤を用いる芳香族ボロン酸のヒドロキシル化反応

    • Author(s)
      野澤 佳菜子
    • Organizer
      第28回有機合成化学セミナー
    • Place of Presentation
      天童
    • Related Report
      2011 Research-status Report
  • [Presentation] ミセル系における芳香族ボロン酸の銅触媒ヒドロキシル化反応

    • Author(s)
      野澤 佳菜子
    • Organizer
      第100回有機合成シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2011 Research-status Report
  • [Presentation] ミセル系におけるアリールボロン酸の酸化的ヒドロキシル化反応

    • Author(s)
      野澤 佳菜子
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2011 Research-status Report
  • [Presentation] 二酸化炭素を用いたシクロカルボキシル化を経由する複素環合成

    • Author(s)
      浅野 成美
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      熊本
    • Related Report
      2011 Research-status Report
  • [Presentation] 遷移金属を用いた分子内炭素-水素結合官能基化プロセスを経由する2-キノロン環構築法の開発

    • Author(s)
      川崎 順平
    • Organizer
      第50回記念日本薬学会東北支部大会
    • Place of Presentation
      仙台
    • Related Report
      2011 Research-status Report
  • [Book] Cross Coupling and Heck-Type Reactions 22012

    • Author(s)
      稲本浄文, 他
    • Publisher
      Thieme
    • Related Report
      2012 Final Research Report
  • [Book] Cross Coupling and Heck-Type Reactions 22012

    • Author(s)
      Kiyofumi Inamoto
    • Publisher
      Thieme
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.pharm.tohoku.ac.jp/~henkan/lab/henkan_top.html

    • Related Report
      2012 Final Research Report
  • [Remarks] 東北大学大学院薬学研究科 分子変換化学分野 ホームページ

    • URL

      http://www.pharm.tohoku.ac.jp/~henkan/lab/publications_lab.html

    • Related Report
      2012 Annual Research Report

URL: 

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

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