Development of Tandem Reactions for Synthesis of Heterocyclic Compounds via Palladium-Catalyzed 1,2-Addition

• Project/Area Number: 20790021
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Nagasaki University
• Principal Investigator: KURIYAMA Masami Nagasaki University, 大学院・医歯薬学総合研究科, 准教授 (40411087)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000); Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: 合成化学 / パラジウム / カルベン / 付加反応 / 複素環 / フタライド

Research Abstract

Novel thioether-imidazolinium carbene ligands were developed and the palladium/thioether-imidazolinium chloride system was proved to be an efficient catalyst for the 1,2-addition reactions of organoboron reagents to aldehydes. This reaction system can be an environmentally benign synthetic method because of its tolerance for aqueous reaction conditions. In addition, efficient synthesis of 3-arylphthalides via palladium-catalyzed 1,2-addition with thioether-imidazolinium carbene ligands was successfully achieved.

Research Products

• [Journal Article] Efficient Synthesis of 3-Arylph-thalides using Palladium-Catalyzed Arylation of Aldehydes with Or-ganoboronic Acids (2009)
  • Author(s): Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Shirai, R.; Onomura, O.
  • Journal Title: J. Org. Chem 74(23) Pages: 9210-9213
  • Peer Reviewed
• [Journal Article] Efficient Synthesis of 3-Arylphthalides using Palladium-Catalyzed Arylation of Aldehydes with Organoboronic Acids (2009)
  • Author(s): Kuriyama, M.
  • Journal Title: J.Org.Chem. 74 Pages: 9210-9213
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed 1, 2-Addition of Potassium Aryl- and Alkenyltri-fluoroborates to Aldehydes using Thioether-Imidazolinium Carbene Ligands (2008)
  • Author(s): Kuriyama, M.; Shimazawa, R.; Enomoto, T.; Shirai, R.
  • Journal Title: J. Org. Chem 73(17) Pages: 6939-6942
  • NAID: 130006998727
  • Peer Reviewed
• [Journal Article] Design and synthesis of N-alkyl oxindolylidene acetic acids as a new class of potent Cdc25A inhibit-tors (2008)
  • Author(s): Shimazawa, R.;Kuriyama, M.; Shirai, R.
  • Journal Title: Bioorg. Med. Chem. Lett. 18(11) Pages: 3350-3353
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed 1,2-Addition of Potassium Aryl-and Alkenyltrifluoroborates to Aldehydes usine Thioether-Imidazolinium Carbene Lieands (2008)
  • Author(s): Kuriyama, M.
  • Journal Title: J. Org. Chem. 73 Pages: 6939-6942
  • Peer Reviewed
• [Journal Article] Design and synthesis of N-alkyl oxindolylidene acetic acids as a new class of potent Cdc25A inhibitors (2008)
  • Author(s): Shimazawa, R.
  • Journal Title: Bioorg. Med. Chem. Lett. 18 Pages: 3350-3353
  • Peer Reviewed
• [Presentation] c-s二座型配位子の開発と遷移金属触媒反応への適用 (2009)
  • Author(s): 栗山正巳
  • Organizer: 有機合成化学協会九州山口支部有機合成化学講演会
  • Place of Presentation: 長崎
  • Year and Date: 2009-11-20
• [Presentation] C-S二座型配位子の開発と遷移金属触媒反応への適用 (2009)
  • Author(s): 栗山正巳
  • Organizer: 有機合成化学協会九州山口支部 有機合成化学講演会
  • Place of Presentation: 長崎大学(長崎)
  • Year and Date: 2009-11-20
• [Presentation] c-s二座型配位子-パラジウム錯体を用いたアルデヒドの触媒的アリール化反応 (2009)
  • Author(s): 栗山正巳
  • Organizer: 第3回万有若手交流合宿セミナー
  • Place of Presentation: 唐津
• [Presentation] Efficient Synthesis of Phthalides using Arylation of Aldehydes with Organoboronic Acids Catalyzed by Palladium/Thioether-Imidazolinium Chloride System (2009)
  • Author(s): Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Shirai, R.; Onomura, O.
  • Organizer: The 11thInternational Kyoto Conferece on New Aspects of Organic Chemistry
  • Place of Presentation: Kyoto, Japan
• [Presentation] 含窒素複素環カルベンを基盤とするC-S二座型配位子を用いたパラジウム触媒による有機ホウ素試薬の付加反応と応用 (2009)
  • Author(s): 栗山正巳, 石山夏希, 榎本光伯, 嶋澤るみ子, 白井隆一, 尾野村治
  • Organizer: 第7回次世代を担う有機化学シンポジウム
  • Place of Presentation: 大阪
• [Presentation] 含窒素複素環カルベンを基盤とするC-S二座型配位子を用いたパラジウム触媒による有機ホウ素試薬の付加反応と応用 (2009)
  • Author(s): 栗山正巳
  • Organizer: 第7回次世代を担う有機化学シンポジウム
  • Place of Presentation: 大阪大学(大阪)
• [Presentation] Efficient Synthesis of Phthalides using Arylation of Aldehydes with Organoboronic Acids Catalyzed by Palladium/Thioether-Imidazolinium Chloride System (2009)
  • Author(s): Kuriyama, M.
  • Organizer: The 11^<th> International Kyoto Conferece on New Aspects of Organic Chemistry
  • Place of Presentation: リーガロイヤルホテル(京都)
• [Presentation] C-S二座型配位子-パラジウム錯体を用いたアルデヒドの触媒的アリール化反応 (2009)
  • Author(s): 栗山正巳
  • Organizer: 第3回万有若手交流合宿セミナー
  • Place of Presentation: 唐津ロイヤルホテル(佐賀)
• [Presentation] C-S二座配位子-パラジウム触媒を用いた有機三フッ化ホウ素塩のアルデヒドへの付加反応 (2008)
  • Author(s): 栗山正巳, 嶋澤るみ子, 榎本光伯, 白井隆一
  • Organizer: 第58回日本薬学会近畿支部大会
  • Place of Presentation: 神戸
  • Year and Date: 2008-10-25
• [Presentation] C-S二座配位子-パラジウム触媒を用いた有機三フッ化ホウ素塩のアルデヒドへの付加反応 (2008)
  • Author(s): 栗山正巳, 嶋澤るみ子, 榎本光伯, 白井隆一
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
• [Presentation] Efficient 1, 2-Addition of Organo-boronic Acids to Aldehydes Catalyzed by the Palladium/Thioether-Imidazo-linium Chloride System (2008)
  • Author(s): Kuriyama, M.; Shimazawa, R.; Shirai, R.
  • Organizer: The Fifth International Symposium on Integrated Synthesis
  • Place of Presentation: Kobe, Japan
• [Presentation] Efficient 1,2-Addition of Organoboronic Acids to Aldehydes Catalyzed by the Palladium/Thioether-Imidazolinium Chloride System (2008)
  • Author(s): Kuriyama, M.
  • Organizer: The Fifth International Symposium on Integrated Synthesis
  • Place of Presentation: Kobe