2014 Fiscal Year Final Research Report
Installation of polar functional groups via carbon -carbon bond cleavage and its application toward the development of functional organic materials
| Project/Area Number |
24550119
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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 | Okayama University |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2015-03-31
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| Keywords | 炭素－炭素結合の切断 / 極性官能基 / 機能性有機材料 / パラジウム / ルイス酸 / イミノニトリル / イミノイソベンゾフラン |
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| Outline of Final Research Achievements |
In this report, PI describes various cyanoformates reacts with arynes and isocyanides in the presence of a cationic palladium catalyst to afford five-membered cyano-substituted iminoisobenzofurans as the major products, along with their isomeric α-iminonitriles as the minor products via three-component coupling reactions. The products obtained from this process are hardly accessible by conventional methods. When the once isolated iminoisobenzofurans are treated with diisobutylaluminum hydride (DIBAL-H) or AlMe3, their transformation into α-iminonitriles is observed.
In addition, an efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavages of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. Generation of isocyanide as the by-product in more thermodynamic manner in DFT calculations also supports the experimental results.
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| Free Research Field |
化学
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