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Production of phenol and resorcinol derivatives using PdC-ethylene system

Research Project

Project/Area Number 15K13758
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Green/Environmental chemistry
Research InstitutionKobe University

Principal Investigator

HAYASHI MASAHIKO  神戸大学, 理学研究科, 教授 (60192704)

Project Period (FY) 2015-04-01 – 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: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsパラジウム触媒 / 酸化反応 / フェノール / レゾルシノール / レスベラトロール / パラジウム / Pd/C / エチレン
Outline of Final Research Achievements

The conversion of cyclohexanone and substituted cyclohexanones to alkyl aryl ethers using a PdC-ethylene system is discussed, where ethylene functions as a hydrogen acceptor. The obtained ethers are easily transformed into the corresponding phenols by treatment with BBr3. Direct conversion of cyclohexenone to phenol in the presence of a catalytic amount of PdC under an ethylene atmosphere.
The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a PdC-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.

Report

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

    (17 results)

All 2017 2016 2015 Other

All Journal Article (6 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 6 results,  Acknowledgement Compliant: 6 results) Presentation (9 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Study on the photo-induced nitric oxide-releasing ability of 4-alkoxy furoxans2017

    • Author(s)
      Matsubara, R.; Takazawa, S.; Ando, A.; Hayashi, M.; Tohda, R.; Tsubaki, M
    • Journal Title

      Asian J. Org. Chem

      Volume: 2017 Issue: 5 Pages: 619-626

    • DOI

      10.1002/ajoc.201700030

    • NAID

      120006414035

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Stynthesis of alkynyl furoxans. Rare carbon-carbon bond forming reaction on a furoxan ring2017

    • Author(s)
      Matsubara, R.; Eguchi, S.; Ando, A.; Hayashi, M
    • Journal Title

      Org. Biomol. Chem

      Volume: 15 Issue: 9 Pages: 1965-1969

    • DOI

      10.1039/c7ob00181a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C Ethylene Catalytic System2017

    • Author(s)
      El-Deeb, I. Y.; Funakoshi, T.; Shimomoto, Y.; Hayashi, M
    • Journal Title

      J. Org. Chem

      Volume: 82 Issue: 5 Pages: 2630-2640

    • DOI

      10.1021/acs.joc.6b03037

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Selective Synthesis of Partially Protected D-Talopyranosides and D-Gulopyranosides via Catalytic Asymmetric Dihydroxylation: Multiplier Effects of Substrate Control and Catalyst Control2016

    • Author(s)
      Namito, Y.; Michigami, K.; Nagahashi, T.; Matsubara, R.; Hayashi, M
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 23 Pages: 6058-6061

    • DOI

      10.1021/acs.orglett.6b03000

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Conversion of Cyclohexanones to Alkyl Aryl Ethers Using a Pd/C Ethylene System2016

    • Author(s)
      El-Deeb, I. Y.; Tian, M.; Funakoshi, T.; Matsubara, R.; Hayashi, M
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2016 Issue: 2 Pages: 409-413

    • DOI

      10.1002/ejoc.201601362

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Concise Synthesis of Asymmetrically 4,5-Disubstituted 9,9-Dimethyl-9H-xanthenes2015

    • Author(s)
      R. Matsubara,* M. Koide, Y.-S. Shin, T. Shimada, M. Hayashi
    • Journal Title

      Synthesis

      Volume: 47 Issue: 02 Pages: 187-192

    • DOI

      10.1055/s-0034-1379368

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] ハロフロキサンの新規合成法の開発と光応答性一酸化窒素ドナーへの応用2016

    • Author(s)
      安藤祥大 松原亮介、髙沢紗緒里、林 昌彦
    • Organizer
      日本化学会 第6回 CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都・江戸川区)
    • Year and Date
      2016-11-11
    • Related Report
      2016 Annual Research Report
  • [Presentation] アルキニル基を有するフロキサン合成法の開発とその応用”2016

    • Author(s)
      江口修平 松原亮介、安藤祥大、林 昌彦
    • Organizer
      日本化学会 第6回 CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都・江戸川区)
    • Year and Date
      2016-11-11
    • Related Report
      2016 Annual Research Report
  • [Presentation] 触媒的不斉ジヒドロキシ化反応を用いた希少糖合成2016

    • Author(s)
      波戸陽一 道上恭佑、永橋孝明、松原亮介、林 昌彦
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢歌劇座(石川県・金沢市)
    • Year and Date
      2016-09-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] Pd/C-エチレン系を用いたレゾルシノール誘導体の脱水素型合成法2016

    • Author(s)
      El-Deeb Ibrahim, 舟越 達哉, 田 苗苗, 松原 亮介, 林 昌彦
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学(東京都・新宿区)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] 触媒的不斉ジヒドロキシ化反応を用いた希少糖合成2016

    • Author(s)
      波戸 陽一・永橋 孝明・道上 恭佑・松原 亮介・林 昌彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学・京都府・京田辺市
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis of 2,3-Unsaturated Sugars Using Aluminium Aryloxide2016

    • Author(s)
      Afiq Md Idros, Yoichi Namito, Ryosuke Matsubara, Masahiko Hayashi
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学・京都府・京田辺市
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Practical synthesis of resorcinol derivatives using Pd/C__ethylene system2016

    • Author(s)
      EL-DEEB, Ibrahim; FUNAKOSHI, Tatsuya; DEN, Tian; MATSUBARA, Ryosuke; HAYASHI, Masahiko
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学・京都府・京田辺市
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 光応答性一酸化窒素ドナーの開発2016

    • Author(s)
      髙沢紗緒里、松原亮介、安藤祥大、林 昌彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学・京都府・京田辺市
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] シアノ基の光感受性保護基の開発2016

    • Author(s)
      馬 慧穎・松原 亮介・林 昌彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学・京都府・京田辺市
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Remarks]

    • URL

      http://www2.kobe-u.ac.jp/~mhayashi/

    • Related Report
      2015 Research-status Report
  • [Patent(Industrial Property Rights)] フロキサン化合物及びその製造方法2015

    • Inventor(s)
      松原亮介、安藤祥大、林 昌彦
    • Industrial Property Rights Holder
      松原亮介、安藤祥大、林 昌彦
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-004799
    • Filing Date
      2015-05-14
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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