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Modular Synthesis of Arylalkanes Using Organosulfur Compounds

Research Project

Project/Area Number 26810056
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Nambo Masakazu  名古屋大学, トランスフォーマティブ生命分子研究所, 特任助教 (10705528)

Research Collaborator CRUDDEN Cathleen M.  クイーンズ大学, 教授
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsアリールアルカン / 炭素-スルホニル結合活性化 / 有機硫黄化合物 / パラジウム触媒 / 逐次的自在合成 / C-H官能基化 / 有機ホウ素化合物 / アゾール / アリール化 / スルホン / スカンジウム触媒 / トリアリールメタン
Outline of Final Research Achievements

We have developed methyl sulfone derivatives as new reacting templates in Pd-catalyzed sequential arylations directed toward the modular synthesis of multiply-arylated methanes. This method enabled the rapid synthesis of thyroid hormone receptor b-selective analog (GC-24) and the development of new inhibitor for plant cell division.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (31 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (4 results) Journal Article (6 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 6 results,  Acknowledgement Compliant: 2 results) Presentation (12 results) (of which Int'l Joint Research: 1 results) Remarks (5 results) Patent(Industrial Property Rights) (4 results) (of which Overseas: 1 results)

  • [Int'l Joint Research] クイーンズ大学(カナダ)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research]

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] クイーンズ大学(カナダ)

    • Related Report
      2015 Research-status Report
  • [Int'l Joint Research]

    • Related Report
      2015 Research-status Report
  • [Journal Article] 1. Development of Versatile Sulfone Electrophiles for Suzuki-Miyaura Cross-Coupling Reactions2017

    • Author(s)
      Masakazu Nambo, Eric C. Keske, Jason P. G. Rygus, Jacky, C.-H. Yim, Cathleen M. Crudden
    • Journal Title

      ACS Catalysis

      Volume: 7 Issue: 2 Pages: 1108-1112

    • DOI

      10.1021/acscatal.6b03434

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Combination of synthetic chemistry and live-cell imaging identified a rapid cell division inhibitor in tobacco and Arabidopsis thaliana2016

    • Author(s)
      Nambo, M., Kurihara, D., Yamada, T., Nishiwaki-Ohkawa, T., Kadofusa, N., Kimata, Y., Kuwata, K., Umeda, M. and Ueda, M.
    • Journal Title

      Plant Cell Physiol.

      Volume: 57 Issue: 11 Pages: 2255-2268

    • DOI

      10.1093/pcp/pcw140

    • NAID

      120006220249

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 4. Arylative Desulfonation of Diarylmethyl Phenyl Sulfones with Arenes Catalyzed by Scandium Triflate2016

    • Author(s)
      Masakazu Nambo, Zachary T. Ariki, Daniel Canseco-Gonzalez, D. Dawson Beattie, Cathleen M. Crudden
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 10 Pages: 2339-2342

    • DOI

      10.1021/acs.orglett.6b00744

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Iterative protecting group-free cross-coupling leading to chiral multiply arylated structures2016

    • Author(s)
      Cathleen M. Crudden, Christopher Ziebenhaus, Jason P. G. Rygus, Kazem Ghozati, Phillip J. Unsworth,Masakazu Nambo, Samantha Both, Marieke Hutchinson, Veronique S. Laberge, Yuuki Maekawa, Daisuke Imao
    • Journal Title

      Nature communication

      Volume: 7 Issue: 1 Pages: 1-7

    • DOI

      10.1038/ncomms11065

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis2015

    • Author(s)
      Masakazu Nambo, Cathleen M. Crudden
    • Journal Title

      ACS catalysis

      Volume: 5 Issue: 8 Pages: 4734-4742

    • DOI

      10.1021/acscatal.5b00909

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri-and Tetraarylmethanes2015

    • Author(s)
      M. Nambo, M. Yar, J.D. Smith, C.M. Crudden
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 1 Pages: 50-53

    • DOI

      10.1021/ol503213z

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] Water-soluble N-heterocyclic carbene protected gold nanoparticles for biological applications2017

    • Author(s)
      Kirsi Salorinne, Renee Man, Henry Li, Masayasu Taki, Masakazu Nambo, Cathleen M. Crudden
    • Organizer
      第97春季年会
    • Place of Presentation
      慶応大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] Enhanced stability: Synthesis and characterizations of N-heterocyclic carbene-stabilized gold nanoparticles2017

    • Author(s)
      Renee Man, Henry Li, Masakazu Nambo, Cathleen M. Crudden
    • Organizer
      第97春季年会
    • Place of Presentation
      慶応大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes2016

    • Author(s)
      Masakazu Nambo, Eric, C. Keske, Jason, P. G. Ryugus, Jacky C.-H. Yim, Cathleen M. Crudden
    • Organizer
      Gordon Research Conference, Stereochemistry
    • Place of Presentation
      Salve Regina University, U.S.
    • Year and Date
      2016-07-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes2016

    • Author(s)
      Masakazu Nambo, Jacky C.-H. Yim, Cathleen M. Crudden
    • Organizer
      第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] Pd-catalyzed Desulfonative Cross-Coupling of Diarylmethyl Sulfones with Oxazoles2016

    • Author(s)
      Jacky C.-H. Yim, Masakazu Nambo, Cathleen M. Crudden
    • Organizer
      第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] Discovery of New Molecules that Control Cell Division and Cell Cycle2016

    • Author(s)
      Masakazu Nambo, Taeko Nishiwaki-Ohkawa, Minako Ueda, Keiko Kuwata, Daisuke Kurihara, Takashi Yoshimura, Tetsuya Higashiyama, Cathleen Crudden
    • Organizer
      2ND CSRS-ITbM Joint Workshop
    • Place of Presentation
      理研(和光キャンパス)
    • Year and Date
      2016-01-07
    • Related Report
      2015 Research-status Report
  • [Presentation] Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes2016

    • Author(s)
      Masakazu Nambo, Jacky C.-H. Yim, Cathleen M. Crudden
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation2015

    • Author(s)
      Masakazu Nambo, Muhammad Yar, Joel D. Smith, Cathleen M. Crudden
    • Organizer
      第95春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Scandium Triflate-Catalyzed Arylative Desulfonation of Diarylmethyl Phenyl Sulfones2015

    • Author(s)
      Zachary, T. Ariki, Masakazu Nambo, Daniel Canseco-Gonzalez, Dawson Beattie, Cathleen M. Crudden
    • Organizer
      第95春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone2014

    • Author(s)
      南保正和, Cathleen M. Crudden
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone2014

    • Author(s)
      Masakazu Nambo, Cathleen M. Crudden
    • Organizer
      IGER International Symposium on Chemical Science in Asia
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-05-26
    • Related Report
      2014 Research-status Report
  • [Presentation] Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone2014

    • Author(s)
      Masakazu Nambo, Cathleen M. Crudden
    • Organizer
      The 2nd International Symposium on Transformative Bio-Molecules
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-05-12
    • Related Report
      2014 Research-status Report
  • [Remarks] 植物の細胞分裂を急速に止める新規化合物の発見

    • URL

      http://www.itbm.nagoya-u.ac.jp/ja/research/2016/11/PCP-Cell-Cycle.php

    • Related Report
      2016 Annual Research Report
  • [Remarks] THREE RINGS STOP CELL DIVISION IN PLANTS

    • URL

      http://www.globalplantcouncil.org/news-and-events/latest-news/three-rings-stop-cell-division-in-plants-development-of-a-triarylmethane-compound-for-possible-control-of-plant-growth

    • Related Report
      2016 Annual Research Report
  • [Remarks] 植物の細胞分裂を急速に止める新規化合物の発見

    • URL

      https://research-er.jp/articles/view/52160

    • Related Report
      2016 Annual Research Report
  • [Remarks] Triarylmethane for control of plant growth

    • URL

      https://phys.org/news/2016-11-triarylmethane-compound-growth.html

    • Related Report
      2016 Annual Research Report
  • [Remarks] Three rings stop cell division in plants

    • URL

      https://www.sciencedaily.com/releases/2016/11/161125084223.htm

    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] 植物細胞分裂抑制剤2016

    • Inventor(s)
      植田美那子、南保正和、栗原大輔、桑田啓子、大川妙子
    • Industrial Property Rights Holder
      植田美那子、南保正和、栗原大輔、桑田啓子、大川妙子
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-028537
    • Filing Date
      2016-02-18
    • Related Report
      2015 Research-status Report
  • [Patent(Industrial Property Rights)] トリ(ヘテロ)アリールアセトニトリルの製造方法2015

    • Inventor(s)
      南保、Yar、Crudden
    • Industrial Property Rights Holder
      南保、Yar、Crudden
    • Industrial Property Rights Type
      特許
    • Filing Date
      2015-12-04
    • Related Report
      2015 Research-status Report
    • Overseas
  • [Patent(Industrial Property Rights)] トリアリールメタン化合物の製造方法2014

    • Inventor(s)
      南保正和, Cathleen Crudden
    • Industrial Property Rights Holder
      南保正和, Cathleen Crudden
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-10-28
    • Related Report
      2014 Research-status Report
  • [Patent(Industrial Property Rights)] トリ(ヘテロ)アリールアセトニトリル化合物の製造方法2014

    • Inventor(s)
      南保, Yar, Crudden
    • Industrial Property Rights Holder
      南保, Yar, Crudden
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-12-12
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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