2013 Fiscal Year Final Research Report
Integrated Radical Reactions
| Project Area | Organic Synthesis based on Integration of Chemical Reactions. New Methodologies and New Materials |
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| Project/Area Number |
21106003
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| Research Category |
Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
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| Allocation Type | Single-year Grants |
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| Review Section |
Science and Engineering
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| Research Institution | Osaka Prefecture University |
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Principal Investigator |
RYU Ilhyong 大阪府立大学, 理学(系)研究科(研究院), 教授 (80210821)
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| Co-Investigator(Kenkyū-buntansha) |
KOBAYASHI Shoji 大阪工業大学, 工学部, 講師 (30374903)
FUKUYAMA Takahide 大阪府立大学, 理学系研究科, 准教授 (60332962)
UEDA Mitsuhiro 大阪府立大学, 理学系研究科, 助教 (60566298)
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| Project Period (FY) |
2009-07-23 – 2014-03-31
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| Keywords | ラジカル反応 / 多成分連結反応 / ジエン合成 / ラクタム合成 / マイクロフロー反応 / ホルムアルデヒド / 集積合成 |
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| Research Abstract |
In this study, we focused on the integrated synthesis by multicomponent radical reactions. We found that radical-bromoallylation of alkynes, allenes, and vinylidenecyclopropanes took place under thermal radical conditions to give good yields of 1,4-, 1,5-, and 1,6-dienes. We also found that using Bu4NBH3CN as a radical mediator, radical reaction of formaldehyde with alkyl halides proceeded well to give hydroxymethylated products. Using tetrakis(tetrabutylammonium)decatungustate, TBADT, as photo-catalyst for C-H functionalization, we achieved the three-component reaction comprising cycloalkanes, CO, and electron-deficient C-C or N-N double bonds, leading to unsymmetrical ketones or amides, respectively. Cycloaddition of terminal alkynes, C-N double bonds, and CO proceeded in the presence of radical mediator, providing a unique access to unsaturated lactams. Continuous flow micro reaction can be applied to living block copolymerization of styrene and butyl acrylate.
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