| Project/Area Number |
26620081
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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 |
Synthetic chemistry
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| Research Institution | Kyoto University |
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Principal Investigator |
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| Research Collaborator |
YAMAMOTO Yutaro 京都大学, 大学院理学研究科, 大学院生
OTSUKA Shinya 京都大学, 大学院理学研究科, 大学院生
NOGI Keisuke 京都大学, 大学院理学研究科, 助教
OSUKA Atsuhiro 京都大学, 大学院理学研究科, 教授
MATSUBARA Hiroshi 大阪府立大学, 大学院理学研究科, 教授
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
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| Keywords | トランスメタル化 / クロスカップリング / パラジウム / ケイ素 / ホウ素 / 塩化アリール / シラトラン / ピナコラートボラン / 還元 / アリール化 / ボリル化 / 有機ケイ素化合物 / 有機ホウ素化合物 / ルイス酸性 |
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| Outline of Final Research Achievements |
Palladium-catalyzed silylation of aryl chlorides with silylsilatranes proceeds under activator-free conditions, hence displaying wide functional group compatibility to allow boryl and siloxy groups to survive. Experimental and computational studies have revealed that smooth transmetalation from silylsilatranes to arylpalladium chloride is facilitated by strong interaction between the Lewis acidic silicon and the chloride.
Similarly, bis(pinacolato)diboron and pinacolatoborane underwent activator-free borylation and reduction of aryl chlorides, respectively, which again takes advantage of strong interaction between the Lewis acidic boron and the chloride.
The cross-coupling reactions of arylsilatranes with aryl chlorides required tetrabutylammonium fluoride as an activator for smooth transmetalation.
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