Development of Systematic Methods for Regioselective Syntheses of Fluorine-Substituted Polycyclic Aromatic Hydrocarbons
| Project/Area Number |
25288016
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (B)
|
| Allocation Type | Partial Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Research Field |
Organic chemistry
|
|---|
| Research Institution | University of Tsukuba |
|---|
Principal Investigator |
|
|---|
| Project Period (FY) |
2013-04-01 – 2016-03-31
|
| Project Status |
Completed (Fiscal Year 2015)
|
| Budget Amount *help |
¥19,370,000 (Direct Cost: ¥14,900,000、Indirect Cost: ¥4,470,000)
Fiscal Year 2015: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Fiscal Year 2014: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Fiscal Year 2013: ¥13,130,000 (Direct Cost: ¥10,100,000、Indirect Cost: ¥3,030,000)
|
|---|
| Keywords | フッ素 / 芳香族化合物 / 縮合環 / カチオン環化 / アルケン / アレン / 求電子的活性化 / 有機半導体 / カルボカチオン / Friedel-Crafts環化 / PAH / アセン / フェナセン / 半導体 / C-F結合活性化 / カチオン / エネルギー準位 / 多環式芳香族炭化水素 / フルオロアルケン / フルオロアレン / トリフルオロメチルアルケン / ドミノ反応 / タンデム反応 |
|---|
| Outline of Final Research Achievements |
Three types of synthetic methods for the regioselectively fluorinated polycyclic aromatic hydrocarbons (F-PAHs) have been developed via Friedel-Crafts-type cyclizations by using electrophilic activation of fluoroalkenes with metal complexes or Lewis acids. When 1,1-difluoro-1-alkenes, 1,1,2-trifluoro-1-alkenes, 1,1-difluoroallenes, and 2-trifluoromethyl-1-alkenes were used as starting materials, the positions of C-C bond formation and fluorine introduction were perfectly controlled by α-cation stabilizing effect of fluorine substituents. Both of these synthetic methods for angular F-PAHs and linear F-PAHs are used in combination to fulfill our objective, systematic syntheses of regioselectively-fluorinated polycyclic aromatic hydrocarbons.
|
Report
(4 results)
Research Products
(110 results)
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
[Journal Article] Redox Switching of Conjugation Length 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 Analogues2013
Author(s)
Suzuki, T.; Tamaoki, H.; Katoono, R.; Fujiwara, K.; Ichikawa, J.; Fukushima, T.
-
Journal Title
Chemistry Letters
Volume: 42
Issue: 7
Pages: 703-705
DOI
NAID
Related Report
Peer Reviewed
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
[Presentation] Generation and Reactions of Perfluoroalkyl-Substituted Organolithiums Using Flow Microreactors2014
Author(s)
Nagaki, A.; Tokuoka, S.; Yamada, S.; Tomida, Y.; Oshiro, K.; Amii, H.; Ichitsuka, T.; Ichikawa, J.; Yoshida, J.
Organizer
13th International Conferences on Microreaction Technology
Place of Presentation
Budapest University of Technology and Economics（Budapest,Hungary）
Year and Date
2014-06-23
Related Report
Int'l Joint Research
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
