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Development of amide transformation by catalytic system inhibiting amide resonance

Research Project

Project/Area Number 25810062
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

Kita Yusuke  大阪大学, 基礎工学研究科, 助教 (40593489)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsアミド結合切断 / エステル化 / 水素化 / アミド変換 / 加アルコール分解
Outline of Final Research Achievements

The amide bond is a ubiquitous and thermodynamically stable due to amide resonance where the lone pair of electrons on the nitrogen is delocalized into the carbonyl. Although amide-directed C-H bond functionalization is an attractive topic of interest, cleavage of the amide bond is difficult owing to the inert nature of amides and thus its application is limited. Under such background, we developed esterification of unactivated amides catalyzed by combined catalytic system of scandium triflate and boron compounds as well as manganese complex bearing N-bidentate ligand. In addition, Ru-catalyzed hydrogenation of amides was efficiently promoted by the addition of catalytic amount of zinc salt.

Report

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

    (11 results)

All 2015 2014 2013 2012

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 3 results) Presentation (5 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results)

  • [Journal Article] Manganese(II) Catalyzed Esterification of N-b-Hydroxyethylamides2015

    • Author(s)
      Nishii Yuji, Akiyama Shoko, Kita Yusuke, Mashima Kazushi
    • Journal Title

      Synlett

      Volume: 26 Issue: 13 Pages: 1831-1834

    • DOI

      10.1055/s-0034-1380428

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hydrogenation of amides catalyzed by a combined catalytic system of a Ru complex with zinc salt2015

    • Author(s)
      Yusuke Kita, Takafumi Higuchi, Kazushi Mashima
    • Journal Title

      Chemical Communications

      Volume: 50 Issue: 76 Pages: 11211-11213

    • DOI

      10.1039/c4cc04481a

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Enhancing Effects of Salt Formation on Catalytic Activity and Enantioselelectivity for Asymmetric Hydrogenation of Isoquinolinium Salts by Dinuclear Halide-Bridged Iridium Complexes Bearing Chiral Diphosphine Ligands2015

    • Author(s)
      Yusuke Kita, Kenta Yamaji, Kosuke Higashida, Sathaiah Kandula, Atsuhiro Iimuro, Kazushi Mashima*
    • Journal Title

      Chemistry A European Journal

      Volume: 21 Issue: 5 Pages: 1915-1927

    • DOI

      10.1002/chem.201405408

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Iridium-catalyzed Asymmetric Hydrogenation of Pyridinium Salts for Constructing Multiple Stereogenic Centers on Piperidines2014

    • Author(s)
      Yusuke Kita, Atsuhiro Iimuro, Shoji Hida, Kazushi Mashima
    • Journal Title

      Chemistry Letter

      Volume: 43 Issue: 3 Pages: 284-286

    • DOI

      10.1246/cl.130943

    • NAID

      130004868004

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Combined Catalytic System of Scandium Triflate and Boronic Ester for Amide Bond Cleavage2013

    • Author(s)
      Y. Kita, Y. Nishii, A. Onoue, K. Mashima
    • Journal Title

      Adv. Synth. Catal.

      Volume: 355 Pages: 3391-3395

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of Isoquinolinium Salts Catalyzed by Chiral Iridium Complexes : Direct Synthesis for Optically Active 1, 2, 3, 4-Tetrahydroisoquinolines2012

    • Author(s)
      Atsuhiro Iimuro
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 7 Pages: 2046-2050

    • DOI

      10.1002/anie.201207748

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Manganese-catalyzed Esterification of Amides2015

    • Author(s)
      Yusuke Kita, Yuji Nishii, Shoko Akiyama, Kazushi Mashima
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都(京都府京都市)
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] イリジウム触媒によるイソキノリン類の不斉水素化反応における基質の塩形成の効果2015

    • Author(s)
      喜多 祐介、山地健太、東田皓介、飯室敦弘、真島和志
    • Organizer
      日本化学会 第95春季年会
    • Place of Presentation
      日本大学 理工学部船橋キャンパス/薬学部
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Lewis Acid-catalyzed Amide Bond Cleavage Reaction2014

    • Author(s)
      喜多 祐介
    • Organizer
      ICOMC 2014 Post-Symposium
    • Place of Presentation
      Icho Kaikan, Osaka University
    • Year and Date
      2014-07-19
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Nickel-catalyzed Amination of Allylic Alcohols2013

    • Author(s)
      Yusuke Kita
    • Organizer
      International Research Training Group “Selectivity in Chemo- and Biocatalysis” Aachen-Osaka Joint Symposium
    • Place of Presentation
      RWTH Aachen, Germany
    • Related Report
      2013 Research-status Report
  • [Presentation] Esterification of -Hydroxyethylamides Catalyzed by Zinc Complex2013

    • Author(s)
      Yusuke Kita
    • Organizer
      17th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Colorado, United States of America
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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