Electrochemical Activation and Synthesis of Organosilicon Compounds

• Project/Area Number: 21750039
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kyoto University
• Principal Investigator: NOKAMI Toshiki 京都大学, 大学院・工学研究科, 講師 (60402963)
• 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: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2009: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
• Keywords: 有機元素化学 / 有機電気化学 / デンドリマー / カルボカチオン / デンドロナイズドポリマー

Research Abstract

We have developed an electrochemical method to generate and accumulate reactive species from organosilicon compounds as a precursor. In this project, we revealed properties of dendritic carbocations and investigated their application for the synthesis of novel dendritic molecules, dendritic reactive species, and dendronized polymers.

Research Products

• [Journal Article] Glycosyl Sulfonium Ions as Storable Intermediates for Glycosylations (2011)
  • Author(s): Nokami, T.; Nozaki, Y.; Saigusa, Y.; Shibuya, A.; Shino Manabe, S.; Ito, Y.; Yoshida, J.
  • Journal Title: Org. Lett. Volume: 13 Issue: 6 Pages: 1544-1547
  • DOI: 10.1021/ol200242u
  • Peer Reviewed
• [Journal Article] Glycosyl Sulfonium Ions as Storable Intermediates for Glycosylations (2011)
  • Author(s): Nokami, T.; Nozaki, Y.; Saigusa, Y.; Shibuya, A.; Manabe, S.; Ito, Y.; Yoshida, J.
  • Journal Title: Org.Lett. Volume: 13 Pages: 1544-1547
  • Peer Reviewed
• [Journal Article] A new highly sterically demanding silyl (TEDAMS) group. Synthesis by multiple substitution of tris(diphenylmethyl)silane with diarylcarbenium ions (2010)
  • Author(s): 寺尾公維、渡邊喬、末廣貴史、野上敏材、吉田潤一
  • Journal Title: Tetrahedron Lett. Volume: Vol.51、No.31 Issue: 31 Pages: 4107-4109
  • DOI: 10.1016/j.tetlet.2010.05.140
  • Peer Reviewed
• [Journal Article] Addition of ArSSAr to Carbon-Carbon Multiple Bonds Using Electrochemistry (2010)
  • Author(s): 藤江駿介、松本浩一、菅誠治、野上敏材、吉田潤一
  • Journal Title: Tetrahedron Volume: Vol.66、No.15 Issue: 15 Pages: 2823-2829
  • DOI: 10.1016/j.tet.2010.02.049
  • NAID: 120002141660
  • Peer Reviewed
• [Journal Article] A new highlysterically demanding silyl (TEDAMS) group. Synthesis by multiple substitution of tris (diphenylmethyl) silane with diarylcarbenium ions (2010)
  • Author(s): Terao, K.; Watabane, T.; Suehiro, T.; Nokami, T.; Yoshida, J.
  • Journal Title: Tetrahedron Lett. Volume: 51 Pages: 4107-4109
  • Peer Reviewed
• [Journal Article] Addition of ArSSAr to Carbon-Carbon Multiple Bonds Using Electrochemistry (2010)
  • Author(s): S.Fujie, et. al.
  • Journal Title: Tetrahedron 66 Pages: 2823-2829
  • Peer Reviewed
• [Journal Article] Addition of ArSSAr to dienes via intramolecular C-C bond formation initiated by a catalytic amount of ArS^+ (2009)
  • Author(s): 松本浩一、菅誠治、野上敏材、吉田潤一
  • Journal Title: Chem. Commun. Volume: No36 Issue: 36 Pages: 5448-5450
  • DOI: 10.1039/b910821a
  • Peer Reviewed
• [Journal Article] Generation of Diarylcarbenium Ion Pools via Electrochemical C-H Bond Dissociation (2009)
  • Author(s): 岡島正幸、曽我和也、渡邊喬、寺尾公維、菅誠治、野上敏材、吉田潤一
  • Journal Title: Bull. Chem. Soc. Jpn Volume: Vol.83、No.5 Issue: 5 Pages: 594-599
  • DOI: 10.1246/bcsj.82.594
  • NAID: 130004152598
  • Peer Reviewed
• [Journal Article] Generation of Diarylcarbenium Ion Pools via Electrochemial C-H Bond Dissociation (2009)
  • Author(s): M.Okajima, et. al.
  • Journal Title: Bull.Chem.Soc.Jpn. 82 Pages: 594-599
  • Peer Reviewed
• [Journal Article] Addition of ArSSAr to dienes via intramolecular C-C bond formation initiated by a catalytic amount of ArS^+ (2009)
  • Author(s): K.Matsumoto, et. al.
  • Journal Title: Chem.Commun. Pages: 5448-5449
  • Peer Reviewed
• [Presentation] 電解酸化を利用したグリコシルスルホニウムイオンの発生・蓄積とグリコシル化反応 (2011)
  • Author(s): 野上敏材
  • Organizer: 電気化学会第78回大会
  • Place of Presentation: 横浜国立大学(横浜)
• [Presentation] Synthesis of dendronized polymers using dendritic diarylcarbeniun ion pools (2010)
  • Author(s): Nokami, T.; Watanabe, T.; Musya, N.; Yoshida, J
  • Organizer: Pacifichem 2010
  • Place of Presentation: Honolulu, HI.
  • Year and Date: 2010-12-18
• [Presentation] Synthesis of dendronized polymers using dendritic diarylcarbeniun ion pools (2010)
  • Author(s): Toshiki Nokami
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 2010-12-17
• [Presentation] Electroorganic Synthesis of Dendronized Polymers (2010)
  • Author(s): 野上敏材、武者直樹、諸藤達也、渡邊 喬、吉田潤一
  • Organizer: 第27回有機合成化学セミナー
  • Place of Presentation: 舞子ビラ神戸、兵庫
  • Year and Date: 2010-09-03
• [Presentation] Electroorganic Synthesis of Dendronized Polymers (2010)
  • Author(s): 野上敏材
  • Organizer: 第27回有機合成化学セミナー
  • Place of Presentation: 舞子ビラ神戸(神戸)
  • Year and Date: 2010-09-03
• [Presentation] Electrochemical Activation of Thioglycosides Using Bu4NOTf as an Electrolyte for Analysis of Glycosylation Intermediates and Oligosaccharide Synthesis (2010)
  • Author(s): T. Nokami, Y. Nozaki, Y. Saigusa, S. Manabe, Y. Ito, J. Yoshida
  • Organizer: The 25^<th> International Carbohydrate Symposium (ICS-2010)
  • Place of Presentation: Tokyo
  • Year and Date: 2010-08-03
• [Presentation] Electrochemical Activation of Thioglycosides Using Bu_4NOTf as an Electrolyte for Analysis of Glycosylation Intermediates and Oligosaccharide Synthesis (2010)
  • Author(s): Toshiki Nokami
  • Organizer: The 25_<th> International Carbohydrate Symposium (ICS-2010)
  • Place of Presentation: Makuhari Messe International Convention Complex, Tokyo (Chiba)
  • Year and Date: 2010-08-03
• [Presentation] アミノ糖由来のチオグリコシドの電気化学的活性化と立体選択的グリコシル化 (2010)
  • Author(s): 野上敏材、三枝善博、野崎裕貴、眞鍋史乃、伊藤幸成、吉田潤一
  • Organizer: 電気化学会第77回大会
  • Place of Presentation: 富山大学、富山
  • Year and Date: 2010-03-30
• [Presentation] ジアリールカルベニウムイオンプールを用いたマルチアルキル化反応 (2010)
  • Author(s): 野上敏材、渡邊喬、末廣貴史、武者直樹、吉田潤一
  • Organizer: 第90回日本化学会年会
  • Place of Presentation: 近畿大学、大阪
  • Year and Date: 2010-03-26
• [Presentation] ジアリールカルベニウムイオンプールを用いたマルチアルキル化反応 (2010)
  • Author(s): 野上敏材
  • Organizer: 第90回 日本化学会年会
  • Place of Presentation: 近畿大学(東大阪)
  • Year and Date: 2010-03-26
• [Remarks]
  • URL: http://www.sbchem.kyoto-u.ac.jp/yoshida-lab/