Development of transition-metal catalyzed fixation of carbon dioxide via carbon-carbon bond formation

• Project/Area Number: 25708017
• Research Category: Grant-in-Aid for Young Scientists (A)
• Allocation Type: Partial Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Kyoto University
• Principal Investigator: Fujihara Tetsuaki 京都大学, 工学(系)研究科(研究院), 准教授 (30374698)
• Project Period (FY): 2013-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥25,610,000 (Direct Cost: ¥19,700,000、Indirect Cost: ¥5,910,000); Fiscal Year 2016: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2015: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2014: ¥9,230,000 (Direct Cost: ¥7,100,000、Indirect Cost: ¥2,130,000); Fiscal Year 2013: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000)
• Keywords: 二酸化炭素 / 銅 / ニッケル / コバルト / アルキン / アレン / 亜鉛 / コバルト触媒 / アクリル酸エステル / ヒドロシラン / アルコール / カルボン酸 / シリルボラン

Outline of Final Research Achievements

In this research, we have focused on the development of transition-metal catalyzed carboxylation reactions using carbon dioxide via carbon-carbon bond formation. As a result, various carboxylation reactions using cobalt, nickel and copper catalysts were developed.

Research Products

• [Journal Article] Synthesis of Cyclic Carbonates from Epoxides and Carbon Dioxide Catalyzed by MgCl2 (2017)
  • Author(s): T. Fujihara, M. Inokuchi, T. Mizoe, K. Nogi, J. Terao, Y. Tsuji
  • Journal Title: Chem. Lett. Volume: 46
  • NAID: 130005709477
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Transition Metal-catalyzed Fixation of Carbon Dioxide <i>via</i> Carbon–carbon Bond Formation (2016)
  • Author(s): T. Fujihara, Y. Tsuji
  • Journal Title: Journal of the Japan Petroleum Institute Volume: 59 Issue: 3 Pages: 84-92
  • DOI: 10.1627/jpi.59.84
  • NAID: 130005161536
  • ISSN: 1346-8804, 1349-273X
  • Year and Date: 2016-05-01
  • Peer Reviewed
• [Journal Article] Carboxyzincation Employing Carbon Dioxide and Zinc Powder: Cobalt-Catalyzed Multicomponent Coupling Reactions with Alkynes (2016)
  • Author(s): K. Nogi, T. Fujihara, J. Terao, Y. Tsuji
  • Journal Title: J. Am. Chem. Soc. Volume: 138 Issue: 17 Pages: 5547-5550
  • DOI: 10.1021/jacs.6b02961
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Transition-Metal-Catalyzed Fixation of Carbon Dioxide via Carbon-Carbon Bond Formation (2016)
  • Author(s): Tetsuaki Fujihara, Yasushi Tsuji
  • Journal Title: J. Jpn. Petro. Inst. Volume: 59
  • NAID: 130005161536
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Copper-Catalyzed C-C Bond-forming Transformation of CO2 to the Alcohol Oxidation level: Selective Synthesis of Homoallylic Alcohols from Allenes, CO2, and Hydrosilanes (2015)
  • Author(s): Y. Tani, K. Kuga, T. Fujihara, J. Terao, Y. Tsuji
  • Journal Title: Chem. Commun. Volume: 51 Issue: 65 Pages: 13020-13023
  • DOI: 10.1039/c5cc03932k
  • NAID: 120005678178
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Copper-Catalyzed Silylative Allylation of Ketones and Aldehydes Employing Allenes and Silylboranes (2015)
  • Author(s): Tani, Yosuke; Yamaguchi, Tatsuya; Fujihara, Tetsuaki; Terao, Jun; Tsuji, Yasushi
  • Journal Title: Chemistry Letters Volume: 44 Issue: 3 Pages: 271-273
  • DOI: 10.1246/cl.141018
  • NAID: 130004712947
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Cobalt-catalyzed carboxylation of propargyl acetates with carbon dioxide (2014)
  • Author(s): Keisuke Nogi, Tetsuaki Fujihara, Jun Terao, Yasushi Tsuji
  • Journal Title: Chemical Communications Volume: 50 Issue: 86 Pages: 13052-13055
  • DOI: 10.1039/c4cc03644a
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Nickel-Catalyzed Doublecarboxylation of Alkynes Employing Carbon Dioxide (2014)
  • Author(s): Fujihara, Tetsuaki; Horimoto, Yuichiro; Mizoe, Taiga; Sayyed, Fareed Bahsha; Tani, Yosuke; Terao, Jun; Sakaki, Shigeyoshi; Tsuji, Yasushi
  • Journal Title: Organic Letters Volume: 16 Issue: 18 Pages: 4960-4963
  • DOI: 10.1021/ol502538r
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Copper-Catalyzed Regiodivergent Silacarboxylation of Allenes with Carbon Dioxide and a Silylborane (2014)
  • Author(s): Tani, Yosuke; Fujihara, Tetsuaki; Terao, Jun; Tsuji, Yasushi
  • Journal Title: Journal of the American Chemical Society Volume: 136 Issue: 51 Pages: 17706-17709
  • DOI: 10.1021/ja512040c
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Copper-Catalyzed Highly Selective Hydroboration of Allenes and 1,3-Dienes (2013)
  • Author(s): K. Semba, M. Shinomiya, T. Fujihara, J. Terao, Y. Tsuji
  • Journal Title: Chem. Eur. J. Volume: 19(印刷中) Issue: 22 Pages: 7125-7132
  • DOI: 10.1002/chem.201300443
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Formal Hydroacylation of Allenes Employing Acid Chlorides and Hydrosilanes (2013)
  • Author(s): T. Fujihara, K. Tatsumi, J. Terao, Y. Tsuji
  • Journal Title: Org. Lett., Volume: 15 Issue: 9 Pages: 2286-2289
  • DOI: 10.1021/ol400862k
  • Peer Reviewed
• [Journal Article] Copper-Catalyzed Borylation of alpha-Alkoxyallenes with Bis(pinacolato)diboron: Efficient Synthesis of 2-Boryl-1,3-butadienes (2013)
  • Author(s): K. Semba, T. Fujihara, J. Terao, Y. Tsuji
  • Journal Title: Angew. Chem. Int. Ed Volume: 52 Issue: 47 Pages: 12400-12403
  • DOI: 10.1002/anie.201306843
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Reduction of Carboxylic Acids to Aldehydes with Hydrosilanes in the Presence of Pivalic Anhydride (2013)
  • Author(s): T. Fujihara, C. Cong, J. Terao, Y. Tsuji
  • Journal Title: Adv. Synth. Catal. Volume: 355 Issue: 17 Pages: 3420-3424
  • DOI: 10.1002/adsc.201300978
  • Peer Reviewed
• [Presentation] 遷移金属錯体触媒を活用する二酸化炭素固定化反応の開発 (2017)
  • Author(s): 藤原哲晶
  • Organizer: フロンティア機能物質創製センター第３回シンポジウム
  • Place of Presentation: 兵庫県立大学
  • Invited
• [Presentation] Copper-Catalyzed Silacarboxylation of Alkynes and Allenes Using Carbon Dioxide and a Silylborane (2016)
  • Author(s): Tetsuaki Fujihara, Yosuke Tani, Jun Terao, Yasushi Tsuji
  • Organizer: International Symposium on Catalysis and Fine Chemicals 2016
  • Place of Presentation: Taipei
  • Year and Date: 2016-11-11
  • Int'l Joint Research / Invited
• [Presentation] コバルト触媒を活用する二酸化炭素固定化反応の新展開 (2016)
  • Author(s): 藤原哲晶
  • Organizer: 分子研研究会「若い世代が創る次世代型分子触媒の開発とその展望」
  • Place of Presentation: 分子科学研究所
  • Year and Date: 2016-11-10
  • Invited
• [Presentation] 二酸化炭素と亜鉛粉末を用いたコバルト触媒によるアルキンのカルボキシ亜鉛化反応 (2016)
  • Author(s): 藤原哲晶、野木馨介，寺尾潤，辻康之
  • Organizer: 第118回触媒討論会
  • Place of Presentation: 岩手大学
  • Year and Date: 2016-09-21
• [Presentation] Carboxyzincation Employing Carbon Dioxide and Zinc Powder: Cobalt-Catalyzed Multicomponent Coupling Reactions with Alkynes (2016)
  • Author(s): Tetsuaki Fujihara, Keisuke Nogi, Jun Terao, Yasushi Tsuji
  • Organizer: 20th International Symposium on Homogeneous Catalysis, Kyoto
  • Place of Presentation: Kyoto
  • Year and Date: 2016-07-12
  • Int'l Joint Research
• [Presentation] 銅触媒を活用する二酸化炭素固定化反応の開発 (2015)
  • Author(s): 藤原哲晶
  • Organizer: 第３回元素戦略に基づいた触媒設計シンポジウム
  • Place of Presentation: 首都大学東京秋葉原サテライトキャンパス
  • Year and Date: 2015-12-04
  • Invited
• [Presentation] 銅触媒による二酸化炭素とシリルボランを用いた不飽和化合物のシラカルボキシル化反応 (2015)
  • Author(s): 藤原哲晶，谷洋介，寺尾潤，辻康之
  • Organizer: 第108回有機合成シンポジウム
  • Place of Presentation: 早稲田大学
  • Year and Date: 2015-11-05
• [Presentation] 銅触媒による二酸化炭素とシリルボランを用いたアレンのシラカルボキシル化反応 (2015)
  • Author(s): 藤原哲晶，谷洋介，寺尾潤，藤原哲晶
  • Organizer: 第19回ケイ素化学シンポジウム
  • Place of Presentation: ラフォーレ琵琶湖
  • Year and Date: 2015-10-23
• [Presentation] 二酸化炭素を炭素源とするニッケル触媒を用いた内部アルキンのダブルカルボキシル化反応 (2014)
  • Author(s): 藤原哲晶，堀本裕一朗，溝江大我，Fareed Bhasha Sayyed，谷洋介，寺尾潤，榊茂好，辻康之
  • Organizer: 第106回有機合成シンポジウム
  • Place of Presentation: 東京(早稲田大学）
  • Year and Date: 2014-11-06 – 2014-11-07
• [Presentation] コバルト触媒存在下における二酸化炭素を用いたプロパルギルおよびアリルエステルのカルボキシル化反応 (2014)
  • Author(s): 野木馨介，岩﨑和貴，藤原哲晶，寺尾潤，辻康之
  • Organizer: 第61回有機金属化学討論会
  • Place of Presentation: 福岡(九州大学）
  • Year and Date: 2014-09-23 – 2014-09-25
• [Presentation] ニッケル触媒による二酸化炭素を用いたアルキンのダブルカルボキシル化反応 (2014)
  • Author(s): 藤原哲晶，堀本裕一朗，溝江大我，Fareed Bhasha Sayyed，谷洋介，寺尾潤，榊茂好，辻康之
  • Organizer: 第61回有機金属化学討論会
  • Place of Presentation: 福岡(九州大学）
  • Year and Date: 2014-09-23 – 2014-09-25
• [Presentation] 銅触媒存在下アレンのシラカルボキシル化反応における2つの位置異性体の選択的合成 (2014)
  • Author(s): 谷 洋介、藤原哲晶、寺尾 潤、辻 康之
  • Organizer: 第61回有機金属化学討論会
  • Place of Presentation: 福岡(九州大学）
  • Year and Date: 2014-09-23 – 2014-09-25
• [Presentation] 二酸化炭素を炭素源とするニッケル触媒を用いた塩化アリール類のカルボキシル化反応 (2014)
  • Author(s): 藤原哲晶，野木馨介，寺尾 潤，辻 康之
  • Organizer: 石油学会第63回研究発表会
  • Place of Presentation: 東京
  • Year and Date: 2014-05-27 – 2014-05-28
• [Presentation] １価のニッケル中間体を鍵とする触媒的二酸化炭素固定化反応の開発 (2013)
  • Author(s): 藤原哲晶
  • Organizer: 東京大学大学院工学系研究科 化学生命工学専攻 第6回ChemBioハイブリッドレクチャー
  • Place of Presentation: 東京大学
  • Invited
• [Presentation] 炭素-炭素結合形成を伴う触媒的二酸化炭素固定化反応の開発 (2013)
  • Author(s): 藤原哲晶
  • Organizer: 京都大学大学院理学研究科 化学専攻 第2回卓越拠点有機若手ワークショップ
  • Place of Presentation: 京都大学
  • Invited
• [Presentation] 二酸化炭素を有用化学物質へと変換する錯体触媒反応の開拓 (2013)
  • Author(s): 藤原哲晶
  • Organizer: 長崎大学重点研究課題「次世代エネルギー物質科学の基盤構築」講演会
  • Place of Presentation: 長崎大学
  • Invited
• [Presentation] Copper-catalyzed Hydro- and Silacarboxylation of Alkynes Employing Carbon Dioxide (2013)
  • Author(s): Tetsuaki Fujihara, Yosuke Tani, Tinghua Xu, Jun Terao and Yasushi Tsuji
  • Organizer: The 3rd International Symposium on Molecular Activation
  • Place of Presentation: Steamboat Springs
• [Presentation] 銅触媒を用いたアレンへの二酸化炭素固定化反応 (2013)
  • Author(s): 谷洋介、久我一成、藤原哲晶、寺尾 潤、辻 康之
  • Organizer: 第60回 有機金属化学討論会
  • Place of Presentation: 学習院大学
• [Presentation] 二酸化炭素を用いたコバルト触媒存在下における酢酸プロパルギルのカルボキシル化反応 (2013)
  • Author(s): 野木馨介、藤原哲晶、寺尾 潤、辻 康之
  • Organizer: 第60回 有機金属化学討論会
  • Place of Presentation: 学習院大学