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Development of new synthetic reactions based on novel acid catalysts

Research Project

Project/Area Number 22790019
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTokyo University of Pharmacy and Life Science

Principal Investigator

YANAI Hikaru  東京薬科大学, 薬学部, 助教 (10408685)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2010: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords触媒開発 / ブレンステッド酸 / ルイス酸 / 多成分反応 / 有機合成化学 / インジウム / 炭素酸
Research Abstract

Synthetic organic chemistry plays an important role to develop functional chemicals. In this research, to improve the efficiency of chemical synthesis, we successfully developed highly effective acid catalyst containing C-H acid functionality. The carbon acid can be used as one of the most effective catalysts in some reactions using silicon enolates. Furthermore, we found that In(OTf)3 nicely catalyzes novel isocyanide-based multi component reactions.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (47 results)

All 2013 2012 2011 2010

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (36 results)

  • [Journal Article] Reductive alkylation of bis(triflyl)methane through self-promoting formation of easily isolable 1,1-bis(triflyl)alkenes2013

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 17 Pages: 2160-2163

    • DOI

      10.1016/j.tetlet.2013.02.039

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of (Z)-1-fluoro-1-alkenyl carboxylates, carbonates and carbamates through chromium mediated transformation of dibromofluoromethylcarbinyl esters and the reactivity as double acyl group donors2012

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Journal of Fluorine Chemistry

      Volume: 133 Pages: 38-51

    • DOI

      10.1016/j.jfluchem.2011.07.022

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Four component reaction of aldehydes, isocyanides, Me3SiN3, and aliphatic alcohols catalyzed by indium triflate2012

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Issue: 25 Pages: 3161-3164

    • DOI

      10.1016/j.tetlet.2012.04.046

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organic acid induced olefination reaction of lactones2012

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 71 Pages: 8967-8969

    • DOI

      10.1039/c2cc33606e

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A regioselective synthesis of poly-substituted aryl triflones through self-promoting three component reaction2011

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Chemical Communications

      Volume: 47 Issue: 25 Pages: 7245-7247

    • DOI

      10.1039/c1cc12093j

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-free defluorinative alkylation of allylic difluorides through Lewis acid-mediated C-F bond activation2011

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Issue: 23 Pages: 2997-3000

    • DOI

      10.1016/j.tetlet.2011.03.148

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An effective method to introduce carbon acid functionality : 2,2-bis(trifluoromethanesulfonyl)ethylation reaction of arenes2011

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Chemistry-A European Journal

      Volume: 17 Issue: 42 Pages: 11747-11751

    • DOI

      10.1002/chem.201102023

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid2010

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Chemical Communications

      Pages: 8728-8730

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbon acid induced Mukaiyama aldol type reaction of sterically hindered ketones2010

    • Author(s)
      Hikaru Yanai
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 75 Pages: 5375-5378

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A rapid and convergent synthesis of α,α-difluoro-β-hydroxyketones through regiospecific defluorinative alkylation reaction2010

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 2625-2628

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Trihaloacetaldehyde N,O-acetals : Useful building blocks for dihalomethylene compounds2010

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 4530-4541

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 有機酸触媒を用いたラクトンのオレフィン化反応2013

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会 第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] 有機酸触媒を用いたラクトンのオレフィン化反応2012

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会 第133 年会
    • Place of Presentation
      東京
    • Year and Date
      2012-11-06
    • Related Report
      2012 Final Research Report
  • [Presentation] 炭素-フッ素結合活性化を基盤とするフルオロアルケンの合成:官能基化されたジペプチドイソスターの合成研究2012

    • Author(s)
      矢内 光
    • Organizer
      第38回 反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2012-11-06
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis of multiple carbon acids and their catalyst activity in organic reactions2012

    • Author(s)
      Hikaru Yanai
    • Organizer
      20th International Symposium on Fluorine Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2012-07-24
    • Related Report
      2012 Final Research Report
  • [Presentation] Defluorinative allylic substitution reaction via Csp3-F bond activation by aluminium-fluorine interaction2012

    • Author(s)
      Hikaru Yanai
    • Organizer
      20th International Symposium on Fluorine Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2012-07-24
    • Related Report
      2012 Final Research Report
  • [Presentation] Defluorinative azidation reaction of difluoroallyl compounds using silylated azide2012

    • Author(s)
      Hikaru Yanai
    • Organizer
      20th International Symposium on Fluorine Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2012-07-24
    • Related Report
      2012 Final Research Report
  • [Presentation] Highly regioselective synthesis of poly-substituted aryl trifluoromethyl sulfones2012

    • Author(s)
      Hikaru Yanai
    • Organizer
      20th International Symposium on Fluorine Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2012-07-24
    • Related Report
      2012 Final Research Report
  • [Presentation] 1-ビス(トリフリル)エチレンの系内発生を基盤とする新合成反応の開発2012

    • Author(s)
      矢内 光
    • Organizer
      第101回 有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2012-06-06
    • Related Report
      2012 Final Research Report
  • [Presentation] 新しい三成分反応を基盤とするトリフリルアレーン類の位置選択的合成2012

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会第132 年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-30
    • Related Report
      2012 Final Research Report
  • [Presentation] 新しい三成分反応を基盤とするトリフリルアレーン類の位置選択的合成2012

    • Author(s)
      矢内光
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-30
    • Related Report
      2011 Annual Research Report
  • [Presentation] ビス(トリフリル)エチル化反応を用いた超強酸触媒の開発2012

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会第132 年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-29
    • Related Report
      2012 Final Research Report
  • [Presentation] ビス(トリフリル)エチル化反応を用いた超強酸触媒の開発2012

    • Author(s)
      矢内光
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-29
    • Related Report
      2011 Annual Research Report
  • [Presentation] 1,1-ビス(トリフリル)エチレンの系内発生を基盤とする新合成反応の開発2012

    • Author(s)
      矢内 光
    • 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] Synthesis of multiple carbon acids and their catalyst activity in organic reactions2012

    • Author(s)
      Hikaru Yanai
    • Organizer
      20th International Symposium on Fluorine Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Annual Research Report
  • [Presentation] Defluorinative allylic substitution reaction via Csp3-F bond activation by aluminium-fluorine interaction2012

    • Author(s)
      Hikaru Yanai
    • Organizer
      20th International Symposium on Fluorine Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Annual Research Report
  • [Presentation] Defluorinative azidation reaction of difluoroallyl compounds using silylated azide2012

    • Author(s)
      Hikaru Yanai
    • Organizer
      20th International Symposium on Fluorine Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Annual Research Report
  • [Presentation] Highly regioselective synthesis of poly-substituted aryl trifluoromethyl sulfones2012

    • Author(s)
      Hikaru Yanai
    • Organizer
      20th International Symposium on Fluorine Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Annual Research Report
  • [Presentation] 炭素-フッ素結合活性化を基盤とするフルオロアルケンの合成:官能基化されたジペプチドイソスターの合成研究2012

    • Author(s)
      矢内 光
    • 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] 超強酸触媒の開発を指向したアレーン骨格へのビス(トリフリル)メチル基の導入法の開発2011

    • Author(s)
      矢内 光
    • Organizer
      第35回フッ素化学討論会
    • Place of Presentation
      岡山
    • Year and Date
      2011-09-27
    • Related Report
      2012 Final Research Report 2011 Annual Research Report
  • [Presentation] Defluorinative alkylation of allylic difluorides directed to an efficient synthesis of functionalized fluorinated alkenes2011

    • Author(s)
      Hikaru Yanai
    • Organizer
      242nd American Chemical Society National Meeting
    • Place of Presentation
      デンバー,米国
    • Year and Date
      2011-08-30
    • Related Report
      2012 Final Research Report
  • [Presentation] Defluorinative alkylation of allylic difluorides directed to an efficient synthesis of functionalized fluorinated alkenes2011

    • Author(s)
      Hikaru Yanai
    • Organizer
      242nd American Chemical Society National Meeting
    • Place of Presentation
      Denver, CO, USA
    • Year and Date
      2011-08-30
    • Related Report
      2011 Annual Research Report
  • [Presentation] Post-synthetic modification of arenes by bis(triflyl)methyl group directed to development of superacid catalysts2011

    • Author(s)
      Hikaru Yanai
    • Organizer
      242nd American Chemical Society National Meeting
    • Place of Presentation
      デンバー,米国
    • Year and Date
      2011-08-28
    • Related Report
      2012 Final Research Report
  • [Presentation] Post-synthetic modification of arenes by bis(triflyl)methyl group directed to development of superacid catalysts2011

    • Author(s)
      Hikaru Yanai
    • Organizer
      242nd American Chemical Society National Meeting
    • Place of Presentation
      Denver, CO, USA
    • Year and Date
      2011-08-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] 多置換アリールトリフルオロメチルスルホンの合成2011

    • Author(s)
      矢内 光
    • Organizer
      第1回フッ素化学若手の会
    • Place of Presentation
      岐阜
    • Year and Date
      2011-08-01
    • Related Report
      2012 Final Research Report 2011 Annual Research Report
  • [Presentation] 強酸性を呈する多価C-H酸の効率的合成法の開発2011

    • Author(s)
      矢内 光
    • Organizer
      第9回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2011-05-27
    • Related Report
      2012 Final Research Report 2011 Annual Research Report
  • [Presentation] ビス(トリフルオロメタンスルホニル)メタンをC1ソースとするシクロヘキセンの一段階合成2011

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会 第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2012 Final Research Report 2010 Annual Research Report
  • [Presentation] アレーン骨格を利用した多価炭素酸の合成と酸触媒としての利用2011

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会 第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-30
    • Related Report
      2012 Final Research Report 2010 Annual Research Report
  • [Presentation] アルデヒド,イソシアニド,遊離脂肪族アルコールおよびトリメチルシリルアジドの四成分反応2010

    • Author(s)
      矢内 光
    • Organizer
      第36回 反応と合成の進歩シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2010-11-01
    • Related Report
      2012 Final Research Report 2010 Annual Research Report
  • [Presentation] シリルビス(トリフルオロメタンスルホニル)メチドを触媒とするα,β-不飽和アルデヒドへの1,4-付加反応2010

    • Author(s)
      矢内 光
    • Organizer
      第34回 フッ素化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2010-10-18
    • Related Report
      2012 Final Research Report 2010 Annual Research Report
  • [Presentation] Tetrakis(trifluoromethanesulfonyl)propane: highly effective Bronsted acid catalyst for C-C bond forming reactions of 2-silyloxyfurans with carbonyl compounds2010

    • Author(s)
      Hikaru Yanai
    • Organizer
      16th European Symposium on Fluorine Chemistry
    • Place of Presentation
      リュブリャナ,スロベニア
    • Year and Date
      2010-07-22
    • Related Report
      2012 Final Research Report
  • [Presentation] A rapid and convergent synthesis of a,a-difluoroketones through regio-specific defluorinative alkylation of trifluoroacetaldehyde N,O-acetals2010

    • Author(s)
      Hikaru Yanai
    • Organizer
      16th European Symposium on Fluorine Chemistry
    • Place of Presentation
      リュブリャナ,スロベニア
    • Year and Date
      2010-07-22
    • Related Report
      2012 Final Research Report
  • [Presentation] Tetrakis(trifluoromethanesulfonyl)propane : highly effective Bronsted acid catalyst for C-C bond forming reactions of 2-silyloxyfurans with carbonyl compounds2010

    • Author(s)
      Takeo Taguchi
    • Organizer
      16th European Symposium on Fluorine Chemistry
    • Place of Presentation
      リュブリャナ,スロベニア
    • Year and Date
      2010-07-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] A rapid and convergent synthesis of α,α-difluoroketones through regio-specific defluorinative alkylation of trifluoroacetaldehyde N,O-acetals2010

    • Author(s)
      Hikaru Yanai
    • Organizer
      16th European Symposium on Fluorine Chemistry
    • Place of Presentation
      リュブリャナ,スロベニア
    • Year and Date
      2010-07-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] 1,1,3,3-テトラキス(トリフルオロメタンスルホニル)プロパンを用いた炭素-炭素結合形成反応の高度効率化2010

    • Author(s)
      矢内 光
    • Organizer
      第97回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2010-06-18
    • Related Report
      2012 Final Research Report
  • [Presentation] 1,1,3,3-テトラキス(トリフルオロメタンスルホニル)プロパンを用いた炭素-炭素結合形成反応の高度効率化2010

    • Author(s)
      矢内光
    • Organizer
      第97回 有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2010-06-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Development of novel synthetic reactions inspired by fluorine chemistry2010

    • Author(s)
      Hikaru Yanai
    • Organizer
      第8回 日中フッ素化学工業会議
    • Place of Presentation
      東京
    • Year and Date
      2010-06-10
    • Related Report
      2012 Final Research Report 2010 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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