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Cross-Coupling Reactions Based on Catalytically Generated Organometallics via Addition of Metal Species

Research Project

Project/Area Number 26810058
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Semba Kazuhiko  京都大学, 工学研究科, 助教 (30712046)

Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
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: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Keywordsクロスカップリング反応 / 金属協働触媒 / クロスカップリング / パラジウム / 銅 / ヒドロアリール化 / カルボホウ素化 / アリールホウ素化 / アルキン / アルケン / 交差カップリング反応
Outline of Final Research Achievements

Cross-coupling reaction is a versatile method for carbon-carbon bond constructions. Cross-coupling reactions generally require pre-synthesis and purification of organometallics prior to the desired carbon-carbon bond formation. In contrast to the conventional cross-coupling reactions, cross-coupling reactions based on catalytically generated organometallics are more atom- and step-economical. Here, we have developed alkylation and alkenylation of organic electrophiles based on catalytically generated organocoppers via hydrocupration, borylcupration, and carbocupration of alkenes and alkynes. These reactions can afford highly functionalized alkanes and alkenes from readily available starting materials in highly step- and atom-economical manners.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (41 results)

All 2018 2017 2016 2015 2014 Other

All Journal Article (7 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 7 results,  Acknowledgement Compliant: 4 results) Presentation (32 results) (of which Int'l Joint Research: 15 results,  Invited: 5 results) Remarks (2 results)

  • [Journal Article] Hydrogenative Cross-coupling of Internal Alkynes and Aryl Iodides by Palladium/Copper Cooperative Catalysis2018

    • Author(s)
      Kazuhiro Semba, Ryohei Kameyama, Yoshiaki Nakao
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 2 Pages: 213-216

    • DOI

      10.1246/cl.170961

    • NAID

      130006337718

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cross-Coupling Reactions by Cooperative Metal Catalysis2017

    • Author(s)
      Semba Kazuhiko、Nakao Yoshiaki
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 75 Issue: 11 Pages: 1133-1140

    • DOI

      10.5059/yukigoseikyokaishi.75.1133

    • NAID

      130006196253

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Arylboration of Internal Alkynes by Cooperative Palladium/Copper Catalysis2017

    • Author(s)
      Semba Kazuhiko、Yoshizawa Megumi、Ohtagaki Yasuhiro、Nakao Yoshiaki
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 90 Issue: 12 Pages: 1340-1343

    • DOI

      10.1246/bcsj.20170226

    • NAID

      130006250359

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Arylboration of 1-Arylalkenes by Cooperative Nickel/Copper Catalysis2016

    • Author(s)
      Kazuhiko Semba, Yasuhiro Ohtagaki, Yoshiaki Nakao
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 16 Pages: 3956-3959

    • DOI

      10.1021/acs.orglett.6b01675

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Pd/Cu Catalysis2016

    • Author(s)
      Kazuhiko Semba, Kenta Ariyama, Hong Zheng, Ryohei Kameyama, Shigeyoshi Sakaki, Yoshiaki Nakao
    • Journal Title

      Angewandte Chemie International Edition

      Volume: - Issue: 21 Pages: 6275-6279

    • DOI

      10.1002/anie.201511975

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Coppe-Catalyzed Semihydrogenation of Alkynes to Z-alkenes2015

    • Author(s)
      Kazuhiko Semba, Ryohei Kameyama, Yoshiaki Nakao
    • Journal Title

      Synlett

      Volume: 26 Issue: 03 Pages: 318-322

    • DOI

      10.1055/s-0034-1379896

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Arylboration of Alkenes by Cooperative Palladium/Copper Catalysis2014

    • Author(s)
      Kazuhiko Semba, Yoshiaki Nakao
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 21 Pages: 7567-7570

    • DOI

      10.1021/ja5029556

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] パラジウム/銅協働触媒による脂肪族アルケンのアリールホウ素化反応2017

    • Author(s)
      太田垣安宏, 仙波一彦, 中尾佳亮
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] 多元素協働触媒による分子変換反応2017

    • Author(s)
      仙波一彦
    • Organizer
      京都大学テックコネクト新技術説明会2017
    • Place of Presentation
      京都大学
    • Year and Date
      2017-03-10
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] パラジウム/銅協働触媒によるアルケンのカルボアリル化反応2017

    • Author(s)
      多田直樹, 仙波一彦, 中尾佳亮
    • Organizer
      第111回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Reductive Cross-Coupling of Alkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis2017

    • Author(s)
      Kazuhiko Semba, Kenta Ariyama, Hong Zheng, Ryohei Kameyama, Shigeyoshi Sakaki, Yoshiaki Nakao
    • Organizer
      Nordic/Kyoto OMCOS 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Reductive Cross-Coupling of Alkynes and Aryl Iodides with Hydrogen by Cooperative Palladium/Copper Catalysis2017

    • Author(s)
      Ryohei Kameyama, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      The 19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS19)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Carboallylation of Alkenes by Cooperative Palladium/Copper Catalysis2017

    • Author(s)
      Naoki Ohta, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      The 19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS19)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] パラジウム/銅協働触媒による水素を還元剤とするアルキンとヨウ化アリールの還元的クロスカップリング反応2017

    • Author(s)
      亀山亮平, 仙波一彦, 中尾佳亮
    • Organizer
      第6回JACI/GSCシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] パラジウム/銅協働触媒によるアルケンのカルボアリル化反応2017

    • Author(s)
      仙波一彦, 多田直樹, 矢野裕子, 飯塚航平, 中尾佳亮
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] パラジウム/銅協働触媒による脂肪族アルケンのアリールホウ素化反応2017

    • Author(s)
      太田垣安宏, 仙波一彦, 中尾佳亮
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Carboboration of Alkenes and Alkynes by Cooperative Metal Catalysis2017

    • Author(s)
      Kazuhiko Semba
    • Organizer
      8th International Collaborative and Cooperative Chemistry Symposium 2017 (ICCCS-8)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cross-Coupling Reactions by Cooperative Palladium/Copper Catalysis2016

    • Author(s)
      Kazuhiko Semba
    • Organizer
      7th International Collaborative and Cooperative Chemistry Symposium 2016 (ICCCS-7)
    • Place of Presentation
      Beijing (China)
    • Year and Date
      2016-12-16
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Mechanistic Studies on Reductive Cross-Coupling of Alkenes and Aryl Bromides with Hydroplanes by Cooperative Palladium/Copper Catalysis2016

    • Author(s)
      Kazuhiko Semba, Hong Zheng, Ryohei Kameyama, Shigeyoshi Sakaki, Yoshiaki Nakao
    • Organizer
      錯体化学会第66回討論会
    • Place of Presentation
      福岡大学
    • Year and Date
      2016-09-11
    • Related Report
      2016 Research-status Report
  • [Presentation] Cross-Coupling Reactions by Cooperative Pd/Cu Catalysis2016

    • Author(s)
      Kazuhiko Semba
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC) 2016
    • Place of Presentation
      Kuching (Malaysia)
    • Year and Date
      2016-08-16
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Arylboration of Alkenes by Cooperative Nickel/Copper Catalysis2016

    • Author(s)
      Yasuhiro Ohtagaki, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      27th International Conference on Organometallic Chemistry
    • Place of Presentation
      Melbourne (Australia)
    • Year and Date
      2016-07-21
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Reductive Cross-Coupling of Alkynes and Aryl Iodides with Hydrogen by Cooperative Palladium/Copper Catalysis2016

    • Author(s)
      Ryohei Kameyama, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      27th International Conference on Organometallic Chemistry
    • Place of Presentation
      Melbourne (Australia)
    • Year and Date
      2016-07-21
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Allylarylation, Allylalkenylation and Allylmethylation of Alkenes by Cooperative Palladium/Copper Catalysis2016

    • Author(s)
      Naoki Ohta, Yuko Yano, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      20th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Kyoto (Japan)
    • Year and Date
      2016-07-14
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Reductive Cross-Coupling of Alkynes and Aryl Iodides with Hydrogen by Cooperative Palladium/Copper Catalysis2016

    • Author(s)
      Ryohei Kameyama, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      20th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Kyoto (Japan)
    • Year and Date
      2016-07-12
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Arylboration of Alkenes by Cooperative Nickel/Copper Catalysis2016

    • Author(s)
      Yasuhiro Ohtagaki, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      20th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Kyoto (Japan)
    • Year and Date
      2016-07-12
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] パラジウム/銅協働触媒によるアルケンのアリルアリール化反応2016

    • Author(s)
      多田直樹, 矢野裕子, 仙波一彦, 中尾佳亮
    • Organizer
      第5回JACI/GSCシンポジウム
    • Place of Presentation
      ANAクラウンプラザホテル神戸
    • Year and Date
      2016-06-03
    • Related Report
      2016 Research-status Report
  • [Presentation] ニッケル/銅協働触媒によるアルケンのアリールホウ素化反応2016

    • Author(s)
      太田垣安宏, 仙波一彦, 中尾佳亮
    • Organizer
      第5回JACI/GSCシンポジウム
    • Place of Presentation
      ANAクラウンプラザホテル神戸
    • Year and Date
      2016-06-03
    • Related Report
      2016 Research-status Report
  • [Presentation] パラジウム/銅協働触媒による水素を還元剤とするアルキンとヨウ化アリールの還元的クロスカップリング反応2016

    • Author(s)
      亀山亮平, 仙波一彦, 中尾佳亮
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Mechanistic Studies on Hydroarylation of Alkenes by Cooperative Palladium/Copper Catalysis2016

    • Author(s)
      仙波一彦, Zheng Hong, 亀山亮平, 榊茂好, 中尾佳亮
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] ニッケル/銅協働触媒によるアルケンのアリールホウ素化反応2016

    • Author(s)
      太田垣安宏, 仙波一彦, 中尾佳亮
    • 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] パラジウム/銅協働触媒によるクロスカップリング反応2016

    • Author(s)
      仙波一彦
    • Organizer
      京都コモンズ 京都大学工学研究科化学系基礎研究(有機合成)ワークショップ
    • Place of Presentation
      京都市成長産業創造センター(京都府・京都市)
    • Year and Date
      2016-02-24
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Cross-Coupling Reactions by Cooperative Pd/Cu Catalysis2015

    • Author(s)
      Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu (Hawaii)
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Arylboration of Alkenes by Cooperative Pd/Cu Catalysis2015

    • Author(s)
      Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      Kyoto (Japan)
    • Year and Date
      2015-11-12
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Copper-Catalyzed Semihydrogenation of Internal Alkynes2015

    • Author(s)
      Ryohei Kameyama, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      Kyoto (Japan)
    • Year and Date
      2015-11-11
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Pd/Cu協働触媒によるヒドロシランを用いたアルケン及びアルキンのヒドロアリール化反応2015

    • Author(s)
      亀山亮平, 仙波一彦, 有山健太, 中尾佳亮
    • Organizer
      第31回若手化学者のための化学道場
    • Place of Presentation
      淡路夢舞台国際会議場(兵庫県・淡路市)
    • Year and Date
      2015-08-28
    • Related Report
      2015 Research-status Report
  • [Presentation] Copper-Catalyzed Semihydrogenation of Internal Alkynes2015

    • Author(s)
      Ryohei Kameyama, Kazuhiko Semba, Yoshiaki Nakao
    • Organizer
      The 18th Organometallic Chemistry Directed Towards Organic Synthesis IUPAC International Symposium
    • Place of Presentation
      Sitges (Spain)
    • Year and Date
      2015-07-01
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] パラジウム/銅協働触媒によるアルキンのアリールホウ素化反応2015

    • Author(s)
      仙波一彦、吉澤恵、中尾佳亮
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 銅触媒による内部アルキンの部分水素化反応2015

    • Author(s)
      亀山亮平、仙波一彦、中尾佳亮
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] パラジウム/銅協働触媒によるアルケンのアリールホウ素化反応2014

    • Author(s)
      仙波一彦、中尾佳亮
    • 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
    • Related Report
      2014 Research-status Report
  • [Remarks] 論文発表

    • URL

      http://www.npc05.kuic.kyoto-u.ac.jp/npc05/publications

    • Related Report
      2016 Research-status Report 2015 Research-status Report 2014 Research-status Report
  • [Remarks] 学会発表

    • URL

      http://www.npc05.kuic.kyoto-u.ac.jp/npc05/presentation

    • Related Report
      2016 Research-status Report 2015 Research-status Report 2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2019-03-29  

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