Study on Catalytic Radical Reaction Process

• Project/Area Number: 25460028
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Hyogo University of Health Sciences
• Principal Investigator: MIYABE Hideto 兵庫医療大学, 薬学部, 教授 (10289035)
• Co-Investigator(Kenkyū-buntansha): 甲谷 繁 兵庫医療大学, 薬学部, 准教授 (00242529)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000); Fiscal Year 2016: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000); Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: 有機合成 / ラジカル / 光触媒 / 触媒反応 / 還元反応 / 環境調和 / 有機化学 / 触媒 / 合成化学 / 合成反応

Outline of Final Research Achievements

Our laboratory developed the method for the sequential construction of carbon-carbon bonds based on the radical reactions using a photocatalyst in aqueous media. The utility of ruthenium catalyst and rhodamine B as water-soluble photocatalysts was confirmed in aqueous-medium radical addition-cyclization-trapping reactions under visible light irradiation. The electron transfer from rhodamine B in the excited state was studied by the fluorescence quenching of rhodamine B. The use of titanium dioxide adsorbing coumarin dyes successfully extended the UV response of titanium dioxide toward visible light region.

Research Products

• [Journal Article] Direct Photoinduced Electron Transfer from Excited State of Rhodamine B for Carbon-Radical Generation (2015)
  • Author(s): E. Yoshioka, S. Kohtani, T. Jichu, T. Fukazawa, T. Nagai, Y. Takemoto, and H. Miyabe
  • Journal Title: Synlett Volume: 26 Issue: 02 Pages: 265-270
  • DOI: 10.1055/s-0034-1379699
  • Peer Reviewed / Open Access
• [Journal Article] Carbon radical addition-cyclization reaction induced by ruthenium-photocatalyst under visible light irradiation (2015)
  • Author(s): E. Yoshioka, S. Kohtani, E.Tanaka, Y. Hata, and H. Miyabe
  • Journal Title: Tetrahedron Volume: 71 Issue: 5 Pages: 773-781
  • DOI: 10.1016/j.tet.2014.12.068
  • Peer Reviewed / Open Access
• [Journal Article] Photohydrogenation of acetophenone using coumarin dye-sensitized titanium dioxide under visible light irradiation (2015)
  • Author(s): S. Kohtani, M. Mori, E. Yoshioka, H. Miyabe
  • Journal Title: Catalysts Volume: 5 Issue: 3 Pages: 1417-1424
  • DOI: 10.3390/catal5031417
  • Peer Reviewed / Open Access
• [Journal Article] Research and Development of Domino Radical Cyclization Reactions (2015)
  • Author(s): 宮部 豪人, 吉岡 英斗, 甲谷 繁
  • Journal Title: Journal of Synthetic Organic Chemistry, Japan Volume: 73 Issue: 9 Pages: 895-901
  • DOI: 10.5059/yukigoseikyokaishi.73.895
  • NAID: 130005104060
  • ISSN: 0037-9980, 1883-6526
  • Peer Reviewed / Open Access
• [Journal Article] Dye-sensitized photo-hydrogenation of aromatic ketones on titanium dioxide under visible light irradiation (2014)
  • Author(s): S. Kohtani, S. Nishioka, E. Yoshioka, and H. Miyabe
  • Journal Title: Catal. Commun. Volume: 15 Pages: 61-65
  • DOI: 10.1016/j.catcom.2013.09.006
  • Peer Reviewed / Open Access
• [Journal Article] Kinetic study on photocatalytic hydrogenation of acetophenone derivatives on titanium dioxide (2014)
  • Author(s): S. Kohtani, Y. Kamoi, E. Yoshioka, and H. Miyabe
  • Journal Title: Catalysis Science and Technology Volume: 4 Issue: 4 Pages: 1084-1091
  • DOI: 10.1039/c3cy00879g
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Cascade Radical Reactions via Carbon-Carbon/Heteroatom Bond-Forming Process (2014)
  • Author(s): Hideto Miyabe, Yoshiji Takemoto
  • Journal Title: Universal Organic Chemistry Volume: 2 Issue: 1 Pages: 1-9
  • DOI: 10.7243/2053-7670-2-1
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Cascade radical reaction of substrates with a carbon-carbon triple bond as a radical acceptor (2013)
  • Author(s): Hideto Miyabe, Ryuta Asada, Yoshiji Takemoto
  • Journal Title: Beilstein J. Org. Chem. Volume: 9 Pages: 1148-1155
  • DOI: 10.3762/bjoc.9.128
  • Peer Reviewed
• [Journal Article] Photocatalytic Cascade Carbon-Carbon Bond-Forming Radical Reaction in Aqueous Media (2013)
  • Author(s): E. Yoshioka, S. Kohtani, E. Tanaka, and Hideto Miyabe
  • Journal Title: Synlett Volume: 12 Issue: 12 Pages: 1578-1582
  • DOI: 10.1055/s-0033-1339182
  • Peer Reviewed
• [Presentation] Photocatalytic carbon-carbon bond forming reaction in aqueous media (2015)
  • Author(s): 宮部 豪人
  • Organizer: 2015 環太平洋国際化学会議
  • Place of Presentation: ハワイコンベンションセンター（米国ハワイ州ホノルル）
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] ローダミンBの一重項励起状態からの一電子移動を介したラジカル生成と反応 (2015)
  • Author(s): 吉岡 英斗、寺中 孝久、深澤 拓也、長井 豊和、甲谷 繁、宮部 豪人
  • Organizer: 第45回複素環化学討論会
  • Place of Presentation: 早稲田大学国際会議場（東京都新宿区）
  • Year and Date: 2015-11-19
• [Presentation] 色素増感酸化チタン光触媒による芳香族カルボニル化合物の可視光水素化反応 (2014)
  • Author(s): 甲谷 繁、西岡早希、森みづ穂、吉岡 英斗、宮部 豪人
  • Organizer: 2014年光化学討論会
  • Place of Presentation: 北海道大学（北海道札幌市）
  • Year and Date: 2014-10-11 – 2014-10-13
• [Presentation] 酸化チタン上で起こるフッ素化アセトフェノン誘導体の光水素化反応と光脱フッ素化反応に関する考察 (2014)
  • Author(s): 甲谷 繁、黒川 拓哉、吉岡 英斗、宮部 豪人
  • Organizer: 2014年光化学討論会
  • Place of Presentation: 北海道大学（北海道札幌市）
  • Year and Date: 2014-10-11 – 2014-10-13
• [Presentation] ローダミンBの励起一重項状態からの光誘起電子移動： パーフルオロアルキルラジカル有機反応への応用 (2014)
  • Author(s): 吉岡 英斗、甲谷 繁、寺中 孝久、深澤 拓也、長井 豊和、中川 僚太郎、竹本 佳司、宮部 豪人
  • Organizer: 2014年光化学討論会
  • Place of Presentation: 北海道大学（北海道札幌市）
  • Year and Date: 2014-10-11 – 2014-10-13
• [Presentation] 塩化鉄を用いたビシクロラクタム環の構築 (2014)
  • Author(s): 吉岡 英斗、池田 朋子、井元 勇希、吉川 知宏、中野 博明、甲谷 繁、宮部 豪人
  • Organizer: 第44回複素環化学討論会
  • Place of Presentation: 札幌市民ホール（北海道札幌市）
  • Year and Date: 2014-09-10 – 2014-09-12
• [Presentation] 色素増感TiO2光触媒による芳香族ケトン類の可視光水素化反応
  • Author(s): 甲谷 繁、西岡 早希、吉岡 英斗、宮部 豪人
  • Organizer: 第63回日本薬学会近畿支部総会大会
  • Place of Presentation: 同志社女子大学京田辺キャンパス（京都府京田辺市）
• [Presentation] Ru 光酸化還元触媒を用いたラジカルカスケード反応の開発 ―触媒的水中ラジカル反応―
  • Author(s): 吉岡 英斗、田中 絵理、甲谷 繁、宮部 豪人
  • Organizer: 第63回日本薬学会近畿支部総会大会
  • Place of Presentation: 同志社女子大学京田辺キャンパス（京都府京田辺市）
• [Book] Titanium Dioxide-Induced Photocatalytic Reduction for Organic Synthesis in “Titanium Dioxide: Chemical Properties, Applications and Environmental Effects” (2014)
  • Author(s): Shigeru Kohtani, Hideto Miyabe
  • Publisher: Nova Science Pub Inc
• [Remarks] 兵庫医療大学 薬品化学研究室―有機化学・物理化学
  • URL: http://www2.huhs.ac.jp/~h070012h/
• [Remarks] 兵庫医療大学 教員情報
  • URL: http://ofcach.ofc.huhs.ac.jp/hhshp/KgApp?kyoinId=ymgdgygyggm
• [Remarks] 薬品化学研究室―有機化学・物理化学―
  • URL: http://www2.huhs.ac.jp/~h070012h/
• [Remarks] 薬品化学研究室―有機化学・物理化学―
  • URL: http://www2.huhs.ac.jp/~h070012h/