Low-valent Niobium Catalyzed Efficient Transformation Using Simple Alkenes

• Project/Area Number: 21605011
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Element strategy
• Research Institution: Kansai University
• Principal Investigator: OBORA Yasushi 関西大学, 化学生命工学部, 准教授 (50312418)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000); Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 低原子価ニオブ / 1, 3-シクロヘキサジエン / アルケン / 環化付加 / アルキン / ヒドロシラン / 1,3-シクロヘキサジエン / 三成分カップリング / 単純アルケン / 単純アルキン / 均一系触媒 / 環化付加反応 / クロスカップリング / 単純有機化合物

Research Abstract

Transition-metal-catalyzed[2+2+2] cycloaddition of unsaturated compounds has been extensively studied for the formation of various aromatic and unsaturated cyclic compounds. In this study, we reported that thermally stable low-vallent Nb(III) compounds, NbCl_3(DME) or NbCl_5/(TMS)_3SiH provide as an efficient catalysts for the multi-component coupling[2+2+2] intermolecular cycloaddition reaction of terminal alkynes, internal alkynes and alkenes leading to 1, 3-cyclohexadiene derivatives as the desired products in excellent yield and chemo/regioselectivity.

Research Products

• [Journal Article] Active low-valent niobium catalysts from NbCl5 and hydrosilanes for selective intermolecular cycloadditions (2011)
  • Author(s): Y. Satoh, Y. Obora
  • Journal Title: J. Org. Chem Volume: 76 Pages: 8569-8573
  • Peer Reviewed
• [Journal Article] NbCl_3-catalyzed three-component[2+2+2] cycloaddition reaction of terminal alkynes, internal alkynes and alkenes to tetrasubstituted-1, 3-cyclohexadienes (2011)
  • Author(s): Y. Satoh, Y. Obora
  • Journal Title: Org. Lett Volume: 13 Pages: 2568-2571
  • Peer Reviewed
• [Journal Article] Iridium-catalyzed reaction involving transfer hydrogenation, addition, N-heterocyclization, and alkylation using alcohols and diols as key substrates (2011)
  • Author(s): Y. Obora, Y. Ishii
  • Journal Title: Synlett Pages: 30-51
  • Peer Reviewed
• [Journal Article] NbCl_3-catalyzed three-component [2+2+2] cycloaddition reaction of terminal alkynes, internal alkynes and alkenes to tetrasubstituted-1,3-cyclohexadienes (2011)
  • Author(s): Y.Satoh, Y, Obora
  • Journal Title: Org.Lett. Volume: 13 Pages: 2568-2571
  • Peer Reviewed
• [Journal Article] Active low-valent niobium catalysts from NbCl_5 and hydrosilanes for selective intermolecular cycloadditions (2011)
  • Author(s): Y.Satoh, Y.Obora
  • Journal Title: J.Org.Chem. Volume: 76 Issue: 20 Pages: 8569-8573
  • DOI: 10.1021/jo201757w
  • Peer Reviewed
• [Journal Article] Iridium-catalyzed reaction involving transfer hydrogenation, addition, N-heterocyclization, and alkylation using alcohols and diols as key substrates (2011)
  • Author(s): Y.Obora, Y.Ishii
  • Journal Title: Synlett Volume: 1 Pages: 30-51
  • Peer Reviewed
• [Journal Article] NbCl3-catalyzed intermolecular[2+2+2] cycloaddition of alkynes and α, ω-dienes : Highly chemo-and regioselective formation of 5-ω-alkenel-1, 4-substituted-1, 3-cyclohexadiene derivatives (2010)
  • Author(s): Y. Obora, Y. Satoh, Y. Ishii
  • Journal Title: J. Org. Chem Volume: 75 Pages: 6046-6049
  • Peer Reviewed
• [Journal Article] Direct oxidative coupling of benzenes with acrylonitriles to cinnamonitriles catalyzed by Pd(OAc)_2/HPMoV/O_2 system (2010)
  • Author(s): Y. Obora, Y. Okabe, Y. Ishii
  • Journal Title: Org. Biomol. Chem Volume: 8 Pages: 4071-4073
  • Peer Reviewed
• [Journal Article] Direct oxidative coupling of benzenes with acrylonitriles to cinnamonitriles catalyzed by Pd(OAc)_2/HPMoV/O_2 system (2010)
  • Author(s): Y.Obora, Y.Okabe, Y.Ishii
  • Journal Title: Org.Biomol.Chem. Volume: 8 Pages: 4071-4073
  • Peer Reviewed
• [Journal Article] NbCl3-catalyzed intermolecular [2+2+2] cycloaddition of alkynes and a,ω-dienes : Highly chemo-and regioselective formation of 5-ω-alkenel-1,4-sub stituted-1,3-cyclohexadiene derivatives (2010)
  • Author(s): Y.Obora, Y.Satoh, Y.Ishii
  • Journal Title: J.Org.Chem. Volume: 75 Pages: 6046-6049
  • Peer Reviewed
• [Journal Article] Iridium-catalyzed coupling reaction of primary alcohols with 2-alkynes leading to hyfroacylation products (2010)
  • Author(s): S.Hatanaka, Y.Obora, Y.Ishii
  • Journal Title: Chem.Eur.J. 16 Pages: 1883-1888
  • Peer Reviewed
• [Journal Article] Intermolecular aerobic oxidative allylic amination od simple alkenes with diarylamines catalyzed by the Pd(OCOCF_3)_2/NPMoV/O_2 system (2010)
  • Author(s): Y.Shimizu, Y.Obora, Y.Ishii
  • Journal Title: Org.Lett. 12 Pages: 1372-1374
  • Peer Reviewed
• [Journal Article] Iridium-catalyzed coupling reaction of primary alcohols with 1-aryl-1-propynes leading to secondary homoallylic alcohols (2009)
  • Author(s): Y.Obora, S.Hatanaka, Y.Ishii
  • Journal Title: Org.Lett. 11 Pages: 3510-3513
  • Peer Reviewed
• [Journal Article] Intermolecular oxidative amination of olefins with amines catalyzed by Pd(II)/NpMoV/O_2 system (2009)
  • Author(s): Y.Obora, Y.Shimizu, Y.Ishii
  • Journal Title: Org.Lett. 11 Pages: 5058-5061
  • Peer Reviewed
• [Presentation] Development of efficient catalytic transformation using simple olefins and alcohols (2011)
  • Author(s): Y. Obora
  • Organizer: 14th Asian Chemical Congress 2011
  • Place of Presentation: Queen Sirikit National Convention Center, Bangkok, Thailand
  • Year and Date: 2011-09-07
• [Presentation] Development of efficient catalytic transformation using simple olefins and alcohols (2011)
  • Author(s): Y.Obora
  • Organizer: 14th Asian Chemical Congress 2011
  • Place of Presentation: Queen Sirikit National Convention Center, Bangkok, Thailand(招待講演)
  • Year and Date: 2011-09-07
• [Presentation] Coupling reaction of primary alcohols with 2-alkynes catalyzed by iridium complex (2010)
  • Author(s): Y. Obora, S. Hatanaka, Y. Ishii
  • Organizer: 2010 International chemical congress of pacific basin societies
  • Place of Presentation: Hilton Honolulu, Hawaii, USA
  • Year and Date: 2010-12-18
• [Presentation] NbCl_3-catalyzed[2+2+2] ingtrmolecular cycloaddition of alkynes and alkenes leading to 1,3-cyclohexadiene derivatives (2009)
  • Author(s): Y.Obora, K.Takeshita, Y.Sato, Y.Ishii
  • Organizer: The Eleventh International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-11)
  • Place of Presentation: Rihga Hotel, Kyoto, Kyoto
  • Year and Date: 2009-11-11
• [Patent(Industrial Property Rights)] 低原子価前周期金属化合物を用いたアルキンとアルケンからのシクロヘキサジエン類の製造方法 (2010)
  • Inventor(s): 大洞康嗣,佐藤靖
  • Industrial Property Rights Holder: 関西大学
  • Industrial Property Number: 2010-114257
  • Filing Date: 2010-05-18
• [Patent(Industrial Property Rights)] 低原子価前周期金属化合物を用いたアルキンとアルケンからのシクロヘキサジエン類の製造方法 (2010)
  • Inventor(s): 大洞康嗣, 佐藤靖
  • Industrial Property Rights Holder: 関西大学
  • Industrial Property Number: 2010-114257
  • Filing Date: 2010-05-18