Photocatalytic Conversion of Alcohols for Organic Synthesis

• Project/Area Number: 26410115
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Nagoya University
• Principal Investigator: Hiroshi Naka 名古屋大学, 物質科学国際研究センター, 助教 (70431517)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 有機化学 / 光触媒 / アルコール / 有機合成 / アミン / アルデヒド / 半導体光触媒 / 脱水素化 / N-アルキル化 / N-メチルアミン

Outline of Final Research Achievements

This work focused on the photocatalytic conversion of alcohols as a key elementary process in selective organic synthesis. We developed several photocatalytic systems that enable the dehydrogenation of aromatic and aliphatic alcohols to the corresponding aldehydes and the N-alkylation of primary or secondary amines to tertiary amines using alcohols as alkylating reagents. Scope and limitation of these reactions were also clarified.

Research Products

• [Journal Article] Dehydrogenation of Primary Aliphatic Alcohols by Au/TiO2 Photocatalysts (2017)
  • Author(s): Masaki Shibata, Ryoko Nagata, Susumu Saito, Hiroshi Naka
  • Journal Title: Chem. Lett. Volume: 46 Issue: 4 Pages: 580-582
  • DOI: 10.1246/cl.161195
  • NAID: 130005549078
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] N-Methylation of amines with methanol at room temperature (2015)
  • Author(s): Vasily N. Tsarev, Yuna Morioka, Joaquim Caner, Qing Wang, Richiro Ushimaru, Akihiko Kudo, Hiroshi Naka, Susumu Saito
  • Journal Title: Org. Lett. Volume: nd Issue: 10 Pages: 2530-2533
  • DOI: 10.1021/acs.orglett.5b01063
  • Peer Reviewed
• [Presentation] メタノールを用いた光触媒的 N-メチル化反応によるリバスチグミンの合成 (2017)
  • Author(s): 王 呂鳴，森岡 優菜，野依 良治，斎藤 進，中 寛史
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 仙台
  • Year and Date: 2017-03-24
• [Presentation] N-Alkylation of Amines with Alcohols Using Mixed Photocatalytic System (2017)
  • Author(s): Lyuming Wang, Yuna Morioka, Ryoji Noyori, Susumu Saito, Hiroshi Naka
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 慶応義塾大学，横浜
  • Year and Date: 2017-03-16
• [Presentation] Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols for Production of Platform and Fine Chemicals Using Palladium-Loaded Titanium Oxide (2017)
  • Author(s): Yuki Takada, Joaquim Caner, Hiroshi Naka, Ryoji Noyori, Susumu Saito
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 慶応義塾大学，横浜
  • Year and Date: 2017-03-16
• [Presentation] 金担持酸化チタン光触媒による脂肪族一級アルコールの脱水素化反応 (2017)
  • Author(s): 永田 良子，柴田 将宜，野依 良治，斎藤 進，中 寛史
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 慶応義塾大学，横浜
  • Year and Date: 2017-03-16
• [Presentation] Regioselective Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols without Salt Waste Generation (2017)
  • Author(s): Yuki Takada, Joaquim Caner, Hiroshi Naka, Susumu Saito
  • Organizer: IGER 2016年度年次報告会
  • Place of Presentation: 名古屋大学，名古屋
  • Year and Date: 2017-01-13
• [Presentation] Photocatalytic N-Methylation of Amino Acids with Methanol (2017)
  • Author(s): Yuna Morioka, Hiroshi Naka, Susumu Saito
  • Organizer: IGER 2016年度年次報告会
  • Place of Presentation: 名古屋大学，名古屋
  • Year and Date: 2017-01-13
• [Presentation] 水と水素を使う触媒的合成化学 (2016)
  • Author(s): 中 寛史
  • Organizer: IQCE講演会「量子化学で探る化学の最先端2016」
  • Place of Presentation: 東京大学，東京
  • Year and Date: 2016-11-19
  • Invited
• [Presentation] アルコールの光触媒変換に基づく合成化学 (2016)
  • Author(s): 中 寛史
  • Organizer: 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，岡崎
  • Year and Date: 2016-11-10
  • Invited
• [Presentation] N-Methylation of Amines and Transfer Hydrogenolysis of Allyl Alcohols with Methanol via Light-induced C-O Bond Cleavage (2016)
  • Author(s): Hiroshi Naka, Yuna Morioka, Lyuming Wang, Vasily N. Tsarev, Joaquim Caner, Yuki Takada, Akihiko Kudo, Susumu Saito
  • Organizer: International Symposium on C-O Activation (ISCO-2016)
  • Place of Presentation: Himeji, Japan
  • Year and Date: 2016-10-25
  • Int'l Joint Research
• [Presentation] Regioselective Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols without Salt Waste Generation (2016)
  • Author(s): Yuki Takada, Joaquim Caner, Hiroshi Naka, Susumu Saito
  • Organizer: The 6th International IUPAC Conference on Green Chemistry
  • Place of Presentation: Venice, Italy
  • Year and Date: 2016-10-05
  • Int'l Joint Research
• [Presentation] Photocatalytic N-Methylation of Amines with Methanol at Room Temperature (2016)
  • Author(s): Yuna Morioka, Lyuming Wang, Vasily N. Tsarev, Joaquim Caner, Qing Wang, Richiro Ushimaru, Akihiko Kudo, Hiroshi Naka, Susumu Saito
  • Organizer: EuCheMS Chemistry Congress, Seville 2016
  • Place of Presentation: Seville, Spain
  • Year and Date: 2016-09-11
  • Int'l Joint Research
• [Presentation] Photocatalytic N-Alkylation of Amines with Alcohols for Pharmaceutical Synthesis (2016)
  • Author(s): Lyuming Wang, Yuna Morioka, Susumu Saito, Hiroshi Naka
  • Organizer: The 20th Joint Symposium of Core-to-Core Program on Elements Function for Transformative Catalysis and Materials
  • Place of Presentation: Kingston, Canada
  • Year and Date: 2016-06-27
  • Int'l Joint Research
• [Presentation] 酸化チタン光触媒を用いる一級アルコールの脱水素化反応 (2016)
  • Author(s): 中 寛史，柴田 将宣，永田 良子，斎藤 進
  • Organizer: 第35回光がかかわる触媒化学シンポジウム
  • Place of Presentation: 東京工業大学，東京
  • Year and Date: 2016-06-10
• [Presentation] Ag/TiO2光触媒を用いたアミンのN-メチル化反応 (2016)
  • Author(s): 森岡 優菜，王 呂鳴，Vasily N. Tsarev, Joaquim Caner, 王 青, 牛丸 理一郎，工藤 昭彦，中 寛史，斎藤 進
  • Organizer: 第35回光がかかわる触媒化学シンポジウム
  • Place of Presentation: 東京工業大学，東京
  • Year and Date: 2016-06-10
• [Presentation] Photocatalytic C-N Bond Formation at Room Temperature (2016)
  • Author(s): Yuna Morioka, Lyuming Wang, Vasily N. Tsarev, Joaquim Caner, Qing Wang, Richiro Ushimaru, Akihiko Kudo, Ryoji Noyori, Hiroshi Naka, Susumu Saito
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学，京都
  • Year and Date: 2016-03-24
• [Presentation] Regioselective Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols (2016)
  • Author(s): Yuki Takada, Joaquim Caner, Ryoji Noyori, Hiroshi Naka, Susumu Saito
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学，京都
  • Year and Date: 2016-03-24
• [Presentation] Photocatalytic N-Methylation of Amines at Room temperature (2016)
  • Author(s): Yuna Morioka, Lyuming Wang, Vasily N. Tsarev, Joaquim Caner, Qing Wang, Richiro Ushimaru, Akihiko Kudo, Hiroshi Naka, Susumu Saito
  • Organizer: The 5th International Conference on MEXT project of Integrated Research on Chemical Synthesis
  • Place of Presentation: Nagoya, Japan
  • Year and Date: 2016-01-29
  • Int'l Joint Research
• [Presentation] Photocatalytic N-Methylation of Amines with Methanol (2016)
  • Author(s): Yuna Morioka, Lyuming Wang, Vasily N. Tsarev, Joaquim Caner, Qing Wang, Richiro Ushimaru, Akihiko Kudo, Hiroshi Naka, Susumu Saito
  • Organizer: IGER 2015年度年次報告会
  • Place of Presentation: 名古屋大学，名古屋
  • Year and Date: 2016-01-08
• [Presentation] 持続可能な社会の基礎となる新しい合成化学の開拓 (2015)
  • Author(s): 永田 良子，中 寛史
  • Organizer: 科学三昧 in あいち 2015
  • Place of Presentation: 自然科学研究機構岡崎コンファレンスセンター，岡崎
  • Year and Date: 2015-12-25
• [Presentation] Redox-selective Conversion of Alcohols Using Metal-loaded Photocatalysts (2015)
  • Author(s): Hiroshi Naka, Joaquim Caner, Zijun Liu, Yuki Takada, Aki Matsuoka, Akihiko Kudo, Susumu Saito
  • Organizer: PACIFICHEM 2015
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Photocatalytic N-Methylation of Amines with Methanol for Medicinal Chemistry (2015)
  • Author(s): Yuna Morioka, Lyuming Wang, Vasily Tsarev, Joaquim Caner, Qing Wang, Richiro Ushimaru, Akihiko Kudo, Hiroshi Naka, Susumu Saito
  • Organizer: PACIFICHEM 2015
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Catalytic Conversion of Water and Methanol for Selective Synthesis (2015)
  • Author(s): Hiroshi Naka
  • Organizer: The10th International Conference on Cutting-edge Organic Chemistry in Asia
  • Place of Presentation: Kaohsiung, Taiwan
  • Year and Date: 2015-11-02
  • Int'l Joint Research
• [Presentation] アルコールの光触媒変換に基づく合成化学 (2015)
  • Author(s): 中 寛史
  • Organizer: 統合物質創製化学推進事業第6回若手研究会
  • Place of Presentation: 別府
  • Year and Date: 2015-07-03
• [Presentation] Catalytic Transformation of Alcohols for Selective Organic Synthesis (2015)
  • Author(s): Hiroshi Naka
  • Organizer: Intergroup Seminar at the Laboratory of Organic Chemistry
  • Place of Presentation: ETH Zurich, Switzerland
  • Year and Date: 2015-04-28
  • Int'l Joint Research / Invited
• [Presentation] N-Methylation of amines with methanol at room temperature (2015)
  • Author(s): Y. Morioka, V. N. Vasily, J. Caner, W. Qing, R. Ushimaru, A. Kudo, H. Naka, S. Saito
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 日本大学，船橋 ．
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] 半導体光触媒を用いる酸化・還元の精密有機合成への展開 (2014)
  • Author(s): Caner, Joaquim， Liu, Zijun， 工藤 昭彦， 中 寛史， 斉藤 進
  • Organizer: 2014年光化学討論会
  • Place of Presentation: 北海道大学，札幌
  • Year and Date: 2014-10-11 – 2014-10-13
• [Presentation] アルコールの光触媒変換に基づく有機合成反応の開発 (2014)
  • Author(s): 中 寛史，Liu, Zijun，Caner, Joaquim，工藤 昭彦，斉藤 進
  • Organizer: 第 33 回光がかかわる触媒化学シンポジウム
  • Place of Presentation: 東京理科大学，東京
  • Year and Date: 2014-07-18
• [Presentation] アルコールの光触媒変換による合成化学 (2014)
  • Author(s): 中 寛史
  • Organizer: 日本薬学会東海支部特別講演会
  • Place of Presentation: 愛知学院大学，名古屋
  • Year and Date: 2014-07-11
  • Invited
• [Remarks] 名古屋大学 野依特別研究室
  • URL: http://noy.chem.nagoya-u.ac.jp/
• [Remarks] 化学科の最新論文
  • URL: http://www3.chem.nagoya-u.ac.jp/wordpress/?p=10067
• [Remarks] 化学科の最新論文
  • URL: http://www3.chem.nagoya-u.ac.jp/wordpress/?p=10925
• [Remarks] 名古屋大学理学部化学科 研究紹介
  • URL: http://www3.chem.nagoya-u.ac.jp/wordpress/?p=10067