2012 Fiscal Year Final Research Report
Electrophilic activation and reactivity control of fluorinated alkenes by transition-metal complexes
| Project/Area Number |
23655028
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Organic chemistry
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| Research Institution | University of Tsukuba |
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Principal Investigator |
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| Project Period (FY) |
2011 – 2012
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| Keywords | ジフルオロアルケン / パラジウム / 触媒 / 求電子的活性化 / フッ素 / 多環式芳香族炭化水素 / PAH / 有機半導体 |
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| Research Abstract |
We have found that treatment of 1,1-difluoro-1-alkenes (or 1,1,2-trifluoro-1-alkenes) bearing a biphenyl skeleton with cationic Pd(II) catalysts, generated from palladium(II) chloride and silver salts, smoothly affords fluorinated (or difluorinated) phenanthrene derivatives. In this process, the fluorinated alkene moieties seem to be electrophilically activated through π coordination to Pd(II) center, which promotes Friedel-Crafts-type cyclizations to give the products.Regioselective syntheses of fluorinated polycyclic aromatic hydrocarbons (F-PAHs) have been accomplished by our catalytic process starting from well-designed 1,1-difluoro-1-alkenes.
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[Journal Article] Redox switching of conjugationlength using 9,9,10,10-tetraaryl-9,10-dihydrophenanthrene as an ON/OFF unit: Preparation, X-ray structure, and redox properties of perfluorobiphenyl derivative and its SNAr reactions to π-extended analogues
Author(s)
Suzuki, T.; Tamaoki, H.; Katoono, R; Fujiwara, K.; Ichikawa. J.; Fukushima, T.
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Journal Title
Chem. Lett
Volume: (in press)
URL
Peer Reviewed
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