2011 Fiscal Year Final Research Report
DEVELOPMENT OF EFFICIENT ORGANIC SYNTHESIS INVOLVING ORGANOBORANE AND ORGANOZINC PROMOTED BY TRANSITION METAL CATALYSIS
| Project/Area Number |
21350055
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Nagasaki University |
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Principal Investigator |
KIMURA Masanari 長崎大学, 大学院・工学研究科, 教授 (10274622)
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| Co-Investigator(Kenkyū-buntansha) |
SHIGEMITSU Yasuhiro 長崎大学, 工学研究科, 准教授 (50432969)
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| Project Period (FY) |
2009 – 2011
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| Keywords | 選択的合成 / 有機ホウ素 / 有機亜鉛 / パラジウム / アリル化 / ポリフェノール |
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| Research Abstract |
Triethylborane activates allylic alcohols to formπ-allylpalladium key intermediates by oxidative addition of Pd(0) toward allylic C-O bonds and achieves amphiphilic allylations. Pd catalyzes three-component coupling reaction of allylic alcohol, terminal alkyne, and organoborane to provide(E)-1-substituted 2-alkyl-1, 4-pentadiene involving geminal allylation and alkylation at the acetylenic terminal carbon. Bis-diene undergoes the similar multi-component coupling reaction with acetylene and organoborane involving cyclization of bis.π-allypalladium to form trans-allyl pentadienyl cyclic and hetrocyclic compounds. Furthermore, a combination of Pd catalyst and triethylborane effectively promotes 3-hydroxy-4-pentenoic acid to undergoβ-decarboxylative C-C bond cleavage reaction viaβ-vinyloxapalladacyclopentanone to provide conjugated diene and carbon dioxide.
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Research Products
(56 results)
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[Journal Article] Synthesis, solid-state fluorescence properties, and computational analysis of novel 2-aminobenzo[ 4, 5] thieno[ 3, 2-d] pyrimidine 5, 5-dioxides2012
Author(s)
K. Yokota, M. Hagimori, N. Mizuyama, Y. Nishimura, H. Fujito, Y. Shigemitsu, Y. Tominaga.
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Journal Title
Beilstein Journal of Organic Chemistry
Volume: Vol.8
Pages: 266-274
Peer Reviewed
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