Development of Catalyst Immobilized Micro Reactor for Combinatorial Multi Step Reactions

• Project/Area Number: 21750091
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: The University of Tokyo
• Principal Investigator: UENO Masaharu The University of Tokyo, 大学院・理学系研究科, 助教 (80361509)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2009: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
• Keywords: 合成化学 / 触媒・化学プロセス / マイクロ・ナノデバイス / 酸化反応 / 連続プロセス / 酸素酸化反応

Research Abstract

We have developed a gold-immobilized micro capillary column reactor for the oxidation of alcohols with molecular oxygen. The oxidation of various alcohols proceeded easily to give the corresponding aldehydes and ketones in good to excellent yields. We also developed polymer immobilized chiral sulfoxide for allylation. Moreover, we have developed diastereoselective allylation of aldehydes and allenylation or propargylation of hydrazonoester in aqueous condition which applicable to microsystem.

Research Products

• [Journal Article] Chiral Sc-catalyzed asymmetric Michael reactions of thiols with enones in water (2011)
  • Author(s): M.Ueno, T.Kitanosono, M.Sakai, S.Kobayashi
  • Journal Title: Organic & Biomolecular Chemistry Volume: 9(掲載確定)
  • Peer Reviewed
• [Journal Article] Aldehyde allylation with allylboronates providing a-addition products (2010)
  • Author(s): Shu, Kobayashi, Toshimitsu Endo, Uwe Schneider, Masaharu Ueno
  • Journal Title: Chem.Commun. 46 Pages: 1260-1262
  • Peer Reviewed
• [Journal Article] Silver Oxide as a Novel Catalyst for Carbon?Carbon Bond-Forming b Reactions in Aqueous Media (2010)
  • Author(s): Masaharu Ueno, Arata Tanoue, Shu, Kobayashi
  • Journal Title: Chem Lett. 39 Pages: 652-653
  • Peer Reviewed
• [Journal Article] Copper(II) and Bismuth(III) Hydroxide-catalyzed Addition Reactions of Hydrazonoester with Allenylboronate in Aqueous Media (2010)
  • Author(s): Shu Kobayashi, Taku Kitanaosono, Masaharu Ueno
  • Journal Title: Synlett. Pages: 2033-2036
  • Peer Reviewed
• [Journal Article] Silver Oxide as a Novel Catalyst for Carbon-Carbon Bond-Forming Reactions in Aqueous Media (2010)
  • Author(s): M.Ueno, A.Tanoue, S.Kobayashi
  • Journal Title: Chemistry Letters Volume: 39 Pages: 652-653
  • NAID: 10027181960
  • Peer Reviewed
• [Journal Article] Copper(II) and Bismuth(III) Hydroxide-catalyzed Addition Reactions of Hydrazonoester with Allenylboronate in Aqueous Media (2010)
  • Author(s): S.Kobayashi, T.Kitanaosono, M.Ueno
  • Journal Title: Synlett Pages: 2033-2036
  • Peer Reviewed
• [Journal Article] Gold-Immobilized Microchannel Flow Reactor for Oxidation of Alcohols with Molecular Oxygen (2009)
  • Author(s): Naiwei Wang, Tsutomu Matsumoto, Masaharu Ueno, Hiroyuki Miyamura, Shu Kobayashi
  • Journal Title: Angew.Chem.Int.Ed. 48 Pages: 4744-4746
  • Peer Reviewed
• [Journal Article] Gold-Immobilized Microchannel Flow Reactor for Oxidation of Alcohols with Molecular Oxygen (2009)
  • Author(s): Wang Naiwei, Matsumoto Tsutomu, Ueno Masaharu, Miyamura Hiroyuki, Shu Kobayashi
  • Journal Title: Angew.Chem., Int.Ed. 48 Pages: 4744-4746
  • Peer Reviewed
• [Presentation] キラルな水酸化亜鉛を触媒とする水系溶媒中でのアルデヒドのα-選択的不斉アリル化反応 (2011)
  • Author(s): 遠藤俊充、上野雅晴、小林修
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学横浜キャンパス
  • Year and Date: 2011-03-28
• [Presentation] 酸化銀(I)を触媒とする水中でのアルデヒドに対するAntiおよびα-選択的アリル化反応 (2011)
  • Author(s): 田上新、上野雅晴、小林修
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学横浜キャンパス
  • Year and Date: 2011-03-28
• [Presentation] 水中での不斉炭素-炭素結合形成反応を指向した多機能触媒の設計と開発 (2011)
  • Author(s): 北之園拓、酒井克、上野雅晴、小林修
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学横浜キャンパス
  • Year and Date: 2011-03-28
• [Presentation] Silver Oxide as a Novel Catalyst for Carbon-Carbon Bond-Forming Reactions in Aqueous Media (2010)
  • Author(s): A.Tanoue, M.Ueno, S.Kobayashi
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies (Pacifichem)
  • Place of Presentation: Honolulu, Hawaii(USA)
  • Year and Date: 2010-12-17
• [Presentation] 新規表面修飾法による耐塩基性を持つ高分子触媒担持型マイクロキャピラリーリアクターの開発及び酸素酸化への応用 (2010)
  • Author(s): 上野雅晴・小林修
  • Organizer: 第21回化学とマイクロ・ナノシステム研究会:講演番号 P-088
  • Place of Presentation: 東京大学小柴ホール(東京)
  • Year and Date: 2010-06-11
• [Presentation] 新規表面修飾法による耐塩基性を持つ高分子触媒担持型マイクロキャピラリーリアクターの開発及び酸素酸化への応用 (2010)
  • Author(s): 上野雅晴、小林修
  • Organizer: 第21回化学とマイクロ・ナノシステム研究会
  • Place of Presentation: 東京大学小柴ホール(東京)
  • Year and Date: 2010-06-11
• [Presentation] 水酸化亜鉛を触媒として用いる水系溶媒中でのアルデヒドに対するSyn およびα-選択的アリル化反応の開発 (2010)
  • Author(s): 遠藤俊充・上野雅晴・小林修
  • Organizer: 日本化学会第90春季年会:講演番号 2F7-08A
  • Place of Presentation: 近畿大学本部キャンパス(大阪)
  • Year and Date: 2010-03-27
• [Presentation] スズから銀へのトランスメタル化を経由する水系溶媒中でのアルデヒドに対するAnti およびα選択的アリル化反応 (2010)
  • Author(s): 田上新・上野雅晴・小林修
  • Organizer: 日本化学会第90春季年会:講演番号 2F7-08A
  • Place of Presentation: 近畿大学本部キャンパス(大阪)
  • Year and Date: 2010-03-27
• [Presentation] 水系溶媒中でのヒドラゾノエステルに対する高選択的アレニル及びプロパルギル付加反応の開発 (2010)
  • Author(s): 上野雅晴・北之園拓・小林修
  • Organizer: 日本化学会第90春季年会:講演番号 1F7-43A
  • Place of Presentation: 近畿大学本部キャンパス(大阪)
  • Year and Date: 2010-03-26
• [Presentation] 金属水酸化物を触媒として用いるイミン等価体に対する水溶液中でのアリル化反応 (2010)
  • Author(s): 上野雅晴・小林修
  • Organizer: 日本化学会第90春季年会:講演番号 1F7-44A
  • Place of Presentation: 近畿大学本部キャンパス(大阪)
  • Year and Date: 2010-03-26
• [Presentation] Gold-Immobilized Microchannel Flow Reactor for Oxidation of Alcohols with Molecular Oxygen (2009)
  • Author(s): Masaharu Ueno, Naiwei Wang, Tsutomu Matsumoto, Hiroyuki Miyamura, Shu Kobayashi
  • Organizer: 16th European Symposium on Organic Chemistry(ESOC 2009)
  • Place of Presentation: Prague, Czech Republic
  • Year and Date: 2009-07-14
• [Presentation] Metal Hydroxide-Catalyzed Highly Stereoselective Formal α-addition-type Allylation Reactions of Aldehydes in Aqueous Media (2009)
  • Author(s): Toshimitsu Endo, Masaharu Ueno, Shu Kobayashi
  • Organizer: 16^<th> European Symposium on Organic Chemistry (ESOC 2009).
  • Place of Presentation: the Municipal House, Prague, Czech Republic
• [Presentation] Gold-Immobilized Microchannel Flow Reactor for Oxidation of Alcohols with Molecular Oxygen (2009)
  • Author(s): Masaharu Ueno, Naiwei Wang, Tsutomu Matsumoto, Hiroyuki Miyamura, Shu Kobayashi
  • Organizer: 16^<th> European Symposium on Organic Chemistry (ESOC 2009).
  • Place of Presentation: the Municipal House, Prague, Czech Republic
• [Presentation] Metal Hydroxide-Catalyzed, Highly Stereoselective α-Addition-type Allylation Reactions of Allylboronates withAldehydes in Aqueous Media (2009)
  • Author(s): Toshimitsu Endo, Masaharu Ueno, Shu Kobayashi
  • Organizer: The 6th International Forum on Chemistry of Functional Organic Chemicals (IFOC-6).
  • Place of Presentation: The University of Tokyo Japan
• [Remarks] ホームページ等
  • URL: http://www.chem.s.u-tokyo.ac.jp/users/synorg/index_J.html
• [Remarks] 研究室HP
  • URL: http://www.chem.s.u-tokyo.ac.jp/users/synorg/index_J.html
• [Remarks] 研究室HP
  • URL: http://www.chem.s.u-tokyo.ac.jp/users/synorg/index_J.html