Development of new visible-light-induced carbon-carbon bond formation using organosulfur compounds and its application to preparation of heteroarenes
| Project/Area Number |
18K05121
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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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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Shizuoka University |
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Principal Investigator |
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| Co-Investigator(Kenkyū-buntansha) |
依田 秀実 静岡大学, 工学部, 教授 (20201072)
高橋 雅樹 静岡大学, 工学部, 教授 (30313935)
藤本 圭佑 静岡大学, 工学部, 助教 (10824542)
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 有機硫黄化合物 / 可視光レドックス触媒 / 二量化 / 脱硫置換反応 / 可視光酸化還元触媒 / 脱硫 / 可視光 / 多置換ヘテロアレーン |
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| Outline of Final Research Achievements |
We investigated new visible-light-induced carbon-carbon bond formations using organosulfur compounds. An oxindole derivative bearing a phenylthio group underwent dehydrogenative carbon-carbon bond formation in the presence of Ru(bpy)3Cl2 under blue LEDs to give the dimeric product in 79% yield, although reactions using other α-phenylthio-carbonyl compounds resulted in no formation of the desired product.
Meanwhile, aryl benzyl sulfones underwent desulfonylative carbon-carbon bond formation with a 4-benzyl dihydropyridine derivative in the presence of a catalytic amount of Ir(ppy)3 and a stoichiometric amount of base under blue LEDs, affording bibenzyl derivatives in good yields. In addition, 3-phenyloxindole derivatives bearing a phenylsulfonyl functionality reacted with the dihydropyridine derivative under the comparable reaction conditions, undergoing desulfonative benzylation in moderate yields.
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| Academic Significance and Societal Importance of the Research Achievements |
硫黄官能基の脱離を伴う炭素－炭素結合形成反応の開発において見出した反応では、ベンジル誘導体およびオキシインドール誘導体の両者において全炭素置換４級炭素骨格の構築に成功している。この骨格は生物活性天然物等の合成において鍵となるものであり、今後の不斉反応への展開により合成困難な天然物の不斉合成への利用が期待される。
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Report
(4 results)
Research Products
(26 results)
