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Development of practicality-oriented synthetic organic reactions using toxic gas surrogates

Research Project

Project/Area Number 15K18834
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

Konishi Hideyuki  静岡県立大学, 薬学部, 講師 (20565618)

Co-Investigator(Renkei-kenkyūsha) MANABE Kei  静岡県立大学, 薬学部, 教授 (00251439)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords毒性ガス / 等価体 / 一酸化炭素 / 二酸化硫黄 / パラジウム / 触媒 / 安全 / 実用的 / 実用
Outline of Final Research Achievements

We have developed safe and practical synthetic organic reactions using "toxic gas surrogates" already developed by our laboratory that could generate toxic gases such as carbon monoxide by chemical reactions. In this study, various catalytic carbonylative reactions by using carbon monoxide surrogates could be realized. In addition, we showed that sulfonamides and sulfinamides could be synthesized with complete selectivity using a known sulfur dioxide surrogate for the first time. These results are highly innovative in terms of converting gas-phase reactions using dangerous toxic gases into safe and efficient liquid-phase reactions using their surrogates, and are expected to be used extensively in the future.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (41 results)

All 2018 2017 2016 2015 Other

All Journal Article (10 results) (of which Peer Reviewed: 9 results,  Acknowledgement Compliant: 3 results) Presentation (29 results) (of which Int'l Joint Research: 4 results,  Invited: 4 results) Remarks (2 results)

  • [Journal Article] Palladium-Catalyzed External-CO-Free Carbonylation of Aryl Bromides Using 2,4,6-Trichlorophenyl Formate2018

    • Author(s)
      Hideyuki Konishi, Tomoyuki Sekino, Kei Manabe
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 66 Issue: 5 Pages: 562-567

    • DOI

      10.1248/cpb.c18-00042

    • NAID

      130006729590

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2018-05-01
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Creation of Novel Toxic Gas Surrogates and the Development of Safe and Facile Catalytic Reactions2018

    • Author(s)
      Hideyuki Konishi
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 66 Issue: 1 Pages: 1-19

    • DOI

      10.1248/cpb.c17-00795

    • NAID

      130006301021

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Adjuvant Effect of Short Chain Triacylglycerol Tributyrin on a Mouse Contact Hypersensitivity Model2018

    • Author(s)
      Kota Sekiguchi, Erina Ogawa, Kohta Kurohane, Hideyuki Konishi, Narumi Mochizuki, Kei Manabe, Yasuyuki Imai
    • Journal Title

      Toxicol. Lett.

      Volume: 284 Pages: 56-62

    • DOI

      10.1016/j.toxlet.2017.11.036

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rapid Formation of Fluoren-9-ones via Palladium-Catalyzed External Carbon Monoxide-Free Carbonylation2018

    • Author(s)
      Hideyuki Konishi, Suguru Futamata, Xi Wang, Kei Manabe
    • Journal Title

      Adv. Synth. Catal.

      Volume: 印刷中 Issue: 9 Pages: 1805-1809

    • DOI

      10.1002/adsc.201800155

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed External-CO-Free Reductive Carbonylation of Bromoarenes2017

    • Author(s)
      Hideyuki Konishi, Masataka Fukuda, Tsuyoshi Ueda, Kei Manabe
    • Journal Title

      Org. Synth.

      Volume: 94 Pages: 66-76

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mechanistic Insight into Weak Base-Catalyzed Generation of Carbon Monoxide from Phenyl Formate and Its Application to Catalytic Carbonylation at Room Temperature without Use of External Carbon Monoxide Gas2017

    • Author(s)
      Konishi Hideyuki、Matsubara Mika、Mori Keisuke、Tokiwa Takaki、Arulmozhiraja Sundaram、Yamamoto Yuta、Ishikawa Yoshinobu、Hashimoto Hiroshi、Shigeta Yasuteru、Tokiwa Hiroaki、Manabe Kei
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 359 Issue: 20 Pages: 3592-3601

    • DOI

      10.1002/adsc.201700751

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate2017

    • Author(s)
      Hideyuki Konishi, Hiromichi Tanaka, Kei Manabe
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 7 Pages: 1578-1581

    • DOI

      10.1021/acs.orglett.7b00402

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Practical Synthesis of Axially Chiral Dicarboxylates <i>via</i> Pd-Catalyzed External-CO-Free Carbonylation2016

    • Author(s)
      Hideyuki Konishi, Fumika Hoshino, Kei Manabe
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 10 Pages: 1438-1441

    • DOI

      10.1248/cpb.c16-00486

    • NAID

      130005598055

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 白金触媒でアミンの末端C-H結合を酸化2016

    • Author(s)
      小西英之
    • Journal Title

      化学

      Volume: 71(2) Pages: 62-63

    • Related Report
      2015 Research-status Report
  • [Journal Article] Practical Synthetic Methods Utilizing Formic Acid Derivatives as Carbon Monoxide Sources2015

    • Author(s)
      小西英之、眞鍋敬
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 73 Issue: 9 Pages: 911-922

    • DOI

      10.5059/yukigoseikyokaishi.73.911

    • NAID

      130005104062

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 新規毒性ガス等価体の創出およびこれを用いる実用性志向型触媒的有機合成反応の開発2018

    • Author(s)
      小西英之
    • Organizer
      平成29年度第2回化学系若手研究者講話
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 新規CO等価体を用いるCO挿入を伴う還元的クロスカップリングの開発2018

    • Author(s)
      上原尚也、小西英之、眞鍋敬
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 二酸化硫黄等価体を用いる環状スルホンアミドおよびスルフィンアミド類の選択的合成法の開発2017

    • Author(s)
      田中寛康、小西英之、眞鍋 敬
    • Organizer
      第15回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京・長井記念ホール
    • Year and Date
      2017-05-26
    • Related Report
      2016 Research-status Report
  • [Presentation] 新規毒性ガス等価体の創出と安全かつ簡便な触媒反応の開発2017

    • Author(s)
      小西英之
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台・仙台国際センター
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] ギ酸誘導体を用いる還元的カルボニル化によるアルデヒドのグラムスケール合成2017

    • Author(s)
      福田匡貴、小西英之、眞鍋 敬
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台・東北大学
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] ギ酸フェニルを一酸化炭素源として用いるPd触媒的フルオレノン類合成法の開発2017

    • Author(s)
      二俣 傑、小西英之、眞鍋 敬
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台・東北大学
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] ギ酸2,4,6-トリクロロフェニルを用いるブロモアレーン類の実用的カルボニル化反応の開発2017

    • Author(s)
      関野智行、小西英之、眞鍋 敬
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台・仙台国際センター
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 二酸化硫黄等価体を用いる環状スルホンアミドおよびスルフィンアミド類の選択的合成法の開発2017

    • Author(s)
      田中寛康、小西英之、眞鍋敬
    • Organizer
      第15回次世代を担う有機化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] ギ酸2,4,6-トリクロロフェニルを一酸化炭素源として用いるブロモアレーン類の実用的カルボニル化反応の開発2017

    • Author(s)
      関野智行、小西英之、眞鍋敬
    • Organizer
      第63回日本薬学会東海支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 毒性ガス等価体を用いる実用性指向型有機合成反応の開発2017

    • Author(s)
      小西英之
    • Organizer
      第1回触発型有機化学研究会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ギ酸2,4,6-トリクロロフェニルを一酸化炭素源とするブロモアレーン類の実用的カルボニル化反応の開発2017

    • Author(s)
      関野智行、小西英之、眞鍋 敬
    • Organizer
      第63回日本薬学会東海支部総会・大会
    • Place of Presentation
      岐阜・岐阜薬科大学
    • Related Report
      2016 Research-status Report
  • [Presentation] 二酸化硫黄等価体を用いる環状スルホンアミド及びスルフィンアミド類の一段階合成法の開発2016

    • Author(s)
      田中寛康、小西英之、眞鍋 敬
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      東京・タワーホール船堀
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] Practical Carbonylation Enabled by Carbon Monoxide Surrogates2016

    • Author(s)
      Hideyuki Konishi, Kei Manabe
    • Organizer
      The 16th Tateshina Conference on Organic Chemistry
    • Place of Presentation
      Tateshina Forum (Chino, Nagano)
    • Year and Date
      2016-11-11
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 短鎖脂肪酸グリセロールエステルによる接触性皮膚炎の感作保進作用2016

    • Author(s)
      関口皓太、小川衿菜、小西英之、眞鍋 敬、遠藤由貴奈、黒羽子考太、今井康之
    • Organizer
      フォーラム2016衛生薬学・環境トキシコロジー
    • Place of Presentation
      東京・昭和大学
    • Year and Date
      2016-09-10
    • Related Report
      2016 Research-status Report
  • [Presentation] 毒性ガス等価体を用いる実用性指向型有機合成反応の開発2016

    • Author(s)
      小西英之
    • Organizer
      平成28年度有機合成化学協会東海支部若手研究者のためのセミナー
    • Place of Presentation
      津・三重大学
    • Year and Date
      2016-07-21
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] N-ホルミルサッカリンを一酸化炭素源として用いる還元的カルボニル化によるアルデヒドのグラムスケール合成2016

    • Author(s)
      福田匡貴、小西英之、眞鍋敬
    • Organizer
      第62回日本薬学会東海支部大会
    • Place of Presentation
      名古屋・愛知学院大学
    • Year and Date
      2016-07-09
    • Related Report
      2015 Research-status Report
  • [Presentation] ギ酸誘導体を一酸化炭素源として用いる触媒的フルオレノン類合成法の開発2016

    • Author(s)
      二俣傑、小西英之、眞鍋敬
    • Organizer
      第62回日本薬学会東海支部大会
    • Place of Presentation
      名古屋・愛知学院大学
    • Year and Date
      2016-07-09
    • Related Report
      2015 Research-status Report
  • [Presentation] One-step Synthetic Method of Cyclic Sulfonamides and Sulfinamides Using an SO2 Surrogate2016

    • Author(s)
      Hiromichi Tanaka, Hideyuki Konishi, Kei Manabe
    • Organizer
      The 25th French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Keio Plaza Hotel Tama (Tama, Tokyo)
    • Year and Date
      2016-05-15
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] One-Step Synthetic Method of Cyclic Sulfonamides and Sulfinamides Using an SO2 Surrogate2016

    • Author(s)
      Hiromichi Tanaka, Hideyuki Konishi, Kei Manabe
    • Organizer
      The 25th French-Japanese Symposium on Medicinal and Fine Chemistry (FJS 2016)
    • Place of Presentation
      Tama, Tokyo
    • Year and Date
      2016-05-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ギ酸誘導体をCO源として用いる軸不斉含有ジカルボン酸エステルの効率的合成法の開発2016

    • Author(s)
      星野史佳、小西英之、眞鍋敬
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜・パシフィコ横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 二酸化硫黄等価体を用いるスルフィニル基の直接的導入法の開発2016

    • Author(s)
      田中寛康、小西英之、眞鍋敬
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜・パシフィコ横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] N-ホルミルサッカリンを一酸化炭素源として用いる還元的カルボニル化によるアルデヒドのグラムスケール合成2016

    • Author(s)
      福田匡貴、小西英之、眞鍋 敬
    • Organizer
      第62回日本薬学会東海支部総会・大会
    • Place of Presentation
      名古屋・愛知学院大学
    • Related Report
      2016 Research-status Report
  • [Presentation] ギ酸誘導体を一酸化炭素源として用いる触媒的フルオレノン類合成法の開発2016

    • Author(s)
      二俣 傑、小西英之、眞鍋 敬
    • Organizer
      第62回日本薬学会東海支部総会・大会
    • Place of Presentation
      名古屋・愛知学院大学
    • Related Report
      2016 Research-status Report
  • [Presentation] 毒性ガス等価体を用いる実用性指向型有機合成反応の開発2016

    • Author(s)
      小西英之
    • Organizer
      平成28年度有機合成化学協会東海支部 若手研究者のためのセミナー
    • Place of Presentation
      三重・三重大学
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Mechanistic Study on the Generation of Carbon Monoxide from Phenyl Formate and Its Application to the Development of Pd-Catalyzed Carbonylation at Room Temperature2015

    • Author(s)
      Hideyuki Konishi, Mika Matsubara, Keisuke Mori, Yoshinobu Ishikawa, Hiroshi Hashimoto, Hiroaki Tokiwa, Kei Manabe
    • Organizer
      The 2015 International Chemical Congress of Pacific Basin Societies (Pacifichem 2015)
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ギ酸フェニルをCO源としてい用いる温和な条件下での触媒的カルボニル化反応の開発2015

    • Author(s)
      松原美香、小西英之、眞鍋敬
    • Organizer
      日本病院薬剤師会東海ブロック・日本薬学会東海支部合同学術大会2015
    • Place of Presentation
      名古屋・金城学院大学
    • Year and Date
      2015-11-01
    • Related Report
      2015 Research-status Report
  • [Presentation] 二酸化硫黄等価体を用いる環状スルホンアミドおよびスルフィンアミド類選択的合成法の開発2015

    • Author(s)
      田中寛康、小西英之、眞鍋敬
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      東大阪・近畿大学
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Pd触媒を用いる環状スルホンアミドおよびスルフィンアミド類の一段階合成法の開発2015

    • Author(s)
      田中寛康、小西英之、眞鍋敬
    • Organizer
      第61回日本薬学会東海支部大会
    • Place of Presentation
      名古屋・名古屋市立大学
    • Year and Date
      2015-07-04
    • Related Report
      2015 Research-status Report
  • [Presentation] ギ酸フェニルを一酸化炭素源として用いる環状カルボニル化合物の新規合成法の開発2015

    • Author(s)
      長瀬浩揮、小西英之、眞鍋敬
    • Organizer
      第13回次世代を担う有機化学シンポジウム
    • Place of Presentation
      草津・立命館大学
    • Year and Date
      2015-05-22
    • Related Report
      2015 Research-status Report
  • [Remarks] 静岡県立大学薬学部 医薬品化学分野。薬化学講座 発表論文

    • URL

      http://w3pharm.u-shizuoka-ken.ac.jp/yakka/paper.html

    • Related Report
      2017 Annual Research Report
  • [Remarks] 静岡県立大学薬学部 医薬品化学分野・薬化学講座 発表論文

    • URL

      http://w3pharm.u-shizuoka-ken.ac.jp/yakka/Japanese/paper/paper.html

    • Related Report
      2016 Research-status Report 2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

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