Development of new chemical transformation using properties of nitrogen-nitrogen bonds

• Project/Area Number: 25460011
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Kanazawa University
• Principal Investigator: Taniguchi Tsuyoshi 金沢大学, 薬学系, 助教 (60444204)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000); Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: ヒドラジン / 光延反応 / 鉄触媒 / 酸素 / ラジカル / ボラン / ベンザイン / カルベン / C-H官能基化

Outline of Final Research Achievements

The following new reactions and concepts have been developed: (1) Development of catalytic Mitsunobu reaction using azo reagents recyclable by iron-catalyzed aerobic oxidation; (2) Development of new reactions of alfa-halo hydrazones; (3) Development of direct functionalization of aromatic rings using aryl radicals from anilines; (4) Discovery of hydroboration of benzynes.

Research Products

• [Int'l Joint Research] リュブリャナ大学(スロベニア)
• [Int'l Joint Research] ピッツバーグ大学(米国)
• [Journal Article] Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents (2016)
  • Author(s): Daisuke Hirose, Martin Gozvoda, Janez Kosmrlj, Tsuyoshi Taniguchi
  • Journal Title: Chem. Sci. Volume: 印刷中 Issue: 8 Pages: 5148-5159
  • DOI: 10.1039/c6sc00308g
  • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Aerobic Oxidation of Arylhydrazines with Iron Phthalocyanine (2015)
  • Author(s): Takuma Hashimoto, Daisuke Hirose, Tsuyoshi Taniguchi
  • Journal Title: Advanced Synthesis & Catalysis Volume: 357 Issue: 14-15 Pages: 3346-3352
  • DOI: 10.1002/adsc.201500459
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Hydroboration of Arynes Formed by Hexadehydro－Diels－Alder Cyclizations with N-Heterocyclic Carbene Boranes (2015)
  • Author(s): Takashi Watanabe, Dennis P. Curran, Tsuyoshi Taniguchi
  • Journal Title: Org. Lett. Volume: 17 Issue: 14 Pages: 3450-3453
  • DOI: 10.1021/acs.orglett.5b01480
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Redox Divergent Synthesis of Fawcettimine-Type Lycopodium Alkaloids (2014)
  • Author(s): Hisaaki Zaimoku, Tsuyoshi Taniguchi
  • Journal Title: Chem. Eur, J Volume: 20 Issue: 31 Pages: 9613-9619
  • DOI: 10.1002/chem.201403163
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Hydroboration of Arynes with N-Heterocyclic Carbene Boranes (2014)
  • Author(s): Tsuyoshi Taniguchi, Dennis P. Curran
  • Journal Title: Angew. Chem. Int. Ed. Volume: 53 Issue: 48 Pages: 13150-13154
  • DOI: 10.1002/ange.201408345
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] A New Method for the Synthesis of 1,4-Diols: C(sp3)-H Hydroxylation Induced by Iron-Catalyzed Redox Hydration of Alkenes (2014)
  • Author(s): Tsuyoshi Taniguchi, Daisuke Hirose, Takuma Hashimoto
  • Journal Title: Synlett Volume: 25 Issue: 18 Pages: 2531-2535
  • DOI: 10.1055/s-0034-1379214
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Direct Synthesis of 1,4-Diols from Alkenes by Iron-Catalyzed Aerobic Hydration and C-H Hydroxylation (2014)
  • Author(s): Takuma Hashimoto, Daisuke Hirose, Tsuyoshi Taniguchi
  • Journal Title: Angew. Chem. Int. Ed. Volume: 53 Issue: 10 Pages: 2730-2734
  • DOI: 10.1002/anie.201308675
  • Peer Reviewed
• [Journal Article] Recyclable Mitsunobu Reagents: Catalytic Mitsunobu Reactions with an Iron Catalyst and Atomospheric Oxygen (2013)
  • Author(s): Daisuke Hirose, Tsuyoshi Taniguchi, Hiroyuki Ishibashi
  • Journal Title: Angewandte Chemie International Edition Volume: 52 Issue: 17 Pages: 4613-4617
  • DOI: 10.1002/anie.201300153
  • Peer Reviewed
• [Journal Article] Zaimoku, Hisaaki; Nishide, Hiroshi; Nishibata, Asami; Goto, Naoya; Taniguchi, Tsuyoshi; Ishibashi, Hiroyuki (2013)
  • Author(s): Syntheses of (±)-Serratine, (±)-Lycoposerramine T, and (±)-Lycopoclavamine B
  • Journal Title: Organic Letters Volume: 15 Issue: 9 Pages: 2140-2143
  • DOI: 10.1021/ol400628h
  • Peer Reviewed
• [Journal Article] α-Fluorohydrazones as useful precursors in nucleophilic substitutions (2013)
  • Author(s): Ryota Yunoki, Atsushi Yajima, Tsuyoshi Taniguchi, Hiroyuki Ishibashi
  • Journal Title: Tetrahedron Lett. Volume: 54 Issue: 31 Pages: 4102-4105
  • DOI: 10.1016/j.tetlet.2013.05.110
  • Peer Reviewed
• [Journal Article] Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water (2013)
  • Author(s): Daisuke Hirose, Tsuyoshi Taniguchi
  • Journal Title: Beilstein J. Org. Chem. Volume: 9 Pages: 1713-1717
  • DOI: 10.3762/bjoc.9.196
  • Peer Reviewed
• [Presentation] 空気酸化で再生可能なアゾ試薬を用いる触媒的光延反応の改良と反応機構解析 (2016)
  • Author(s): 廣瀬 大祐, 谷口 剛史, Martin Gozvoda, Janez Kosmrlj
  • Organizer: 日本薬学会第136年会
  • Place of Presentation: 神奈川県横浜市西区みなとみらい1-1-1、パシフィコ横浜
  • Year and Date: 2016-03-26
• [Presentation] Development of New Synthetic Methods Using Iron Phthalocyanine (2015)
  • Author(s): Tsuyoshi Taniguchi
  • Organizer: 7th Pacific Symposium on Radical Chemistry
  • Place of Presentation: Nanyang Technological University (Singapore)
  • Year and Date: 2015-07-15
  • Int'l Joint Research / Invited
• [Presentation] 鉄と酸素を用いる触媒的光延反応の開発 (2015)
  • Author(s): 廣瀬 大祐、橋本 卓磨、谷口 剛史
  • Organizer: 日本化学会第95春季年会2015
  • Place of Presentation: 東京都千代田区神田駿河台1-8-14 日本大学 理工学部船橋キャンパス
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] N－ヘテロサイクリックカルベン－ボラン錯体を用いるベンザイン誘導体のヒドロホウ素化反応 (2015)
  • Author(s): 谷口 剛史、Dennis P. Curran
  • Organizer: 日本薬学会第135年会
  • Place of Presentation: 神戸市中央区港島1-1-3 神戸学院大学
  • Year and Date: 2015-03-26 – 2015-03-28
• [Presentation] （－）-Serratine およびその類縁アルカロイドの不斉合成研究 (2013)
  • Author(s): 材木久晃、谷口剛史
  • Organizer: 第39回反応と合成の進歩シンポジウム
  • Place of Presentation: 福岡県福岡市九州大学医学部百年講堂
• [Remarks] 金沢大学医薬保健研究域薬学系 機能性分子設計学研究室HP
  • URL: http://www.p.kanazawa-u.ac.jp/~gousei/