Development of transformations of bicyclic compounds to monocyclic compounds through sequential bond cleavage
| Project/Area Number |
16K05783
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Tokyo University of Science |
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Principal Investigator |
Matsuda Takanori 東京理科大学, 理学部第一部応用化学科, 准教授 (80359778)
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | 環化 / 骨格転位 / アリール化 / ロジウム / シクロプロペノン / カルボニル化 / 開環 / フラノン / ビインデン / ナフタレン / インドール / アミド / メタセシス / シクロブタン / シクロブテノール / パラジウム / スピロ化合物 / 炭素－炭素結合切断 / シクロブタノール / 触媒 / 合成化学 / 有機化学 / 有機金属化学 / 遷移金属触媒 / 分子変換 |
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| Outline of Final Research Achievements |
In this study, research on catalytic transformations of bicyclic compounds to monocyclic compounds through sequential bond cleavage was conducted, and sevaral reactions were developed. Rh-catalyzed skeletal rearrangements of benzofused spiro[3.3]heptanes gave substituted naphthalenes. Rh-catalyzed carbonylation of (2-pyridylmethylene)cyclobutanes gave five-membered cyclic ketones. Pd-catalyzed ring-opening coupling of cyclobutenols with aryl halides gave γ-arylated α,β-unsaturated ketones. 2-[(2-Azidophenyl)ethynyl]anilines cyclized by Au/Rh relay catalysis to give 5,10-dihydroindolo[3,2-b]indoles. Ag-catalyzed ring-opening [3+2] annulation of cyclopropenones with amides gave 5-amino-2-furanones. Rh-catalyzed addition of arylboronic acids to β-(arylethynyl) ketones gave (arylmethyl)naphthalenes. Ru-catalyzed cycloisomerization of 1,2-bis(2-allylphenyl)ethynes gave 2,2′-dimethyl-3H,3′H-1,1′-biindenes, and tandem RCM of the diynes gave 2,2′-unsubstituted biindenes.
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| Academic Significance and Societal Importance of the Research Achievements |
環歪みを有しユニークな反応性を示すシクロブタン、シクロブテン、シクロプロペン誘導体の新しい遷移金属触媒反応を開発することができた。また、連続的な結合切断反応の持つ合成化学的な有用性を示すこともできた。今後、機能性π共役分子の選択的合成などに応用されることが期待される。さらに、遷移金属触媒による炭素骨格再構築反応の可能性、現時点での課題、および今後の展望についても有益な情報を得ることができた。
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Report
(4 results)
Research Products
(24 results)
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[Presentation] Unusual Transition-Metal-Catalyzed Cycloisomerizations of 2,2′-Dialkynylbiphenyls2016
Author(s)
Takanori Matsuda, Tsuyoshi Goya, Lantao Liu, Kotaro Kato, Yusuke Sakurai, Shoichi Watanuki, Shingo Shimada, Naoki Ishida, Masahiro Murakami
Organizer
International Conference on Chemistry, Chemical Process and Engineering (IC3PE)
Place of Presentation
Yogyakarta, Indonesia
Year and Date
2016-11-15
Related Report
Int'l Joint Research
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