Copper-Catalyzed Trifluoromethylation and Bicyclizations of 1,7-Enynes Leading to Fused Polycycles
A series of trifluoromethyl‐containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin‐fused tetracyclic compounds have been prepared using copper‐catalyzed cascade reaction of benzene‐tethered 1,7‐enynes. A study of the mechanism indicated that radical trifluoromethylation and s...
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| Published in | Advanced synthesis & catalysis Vol. 358; no. 21; pp. 3435 - 3442 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Blackwell Publishing Ltd
03.11.2016
Wiley |
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| Abstract | A series of trifluoromethyl‐containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin‐fused tetracyclic compounds have been prepared using copper‐catalyzed cascade reaction of benzene‐tethered 1,7‐enynes. A study of the mechanism indicated that radical trifluoromethylation and sequential 6‐exo‐dig/5‐endo‐trig bicyclization processes were involved in this protocol. Moreover, some selected products showed certain fungicidal activities against 14 kinds of plant fungi which means that these functionalized tetracyclic compounds might be used in the agrochemical field. |
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| AbstractList | A series of trifluoromethyl‐containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin‐fused tetracyclic compounds have been prepared using copper‐catalyzed cascade reaction of benzene‐tethered 1,7‐enynes. A study of the mechanism indicated that radical trifluoromethylation and sequential 6‐exo‐dig/5‐endo‐trig bicyclization processes were involved in this protocol. Moreover, some selected products showed certain fungicidal activities against 14 kinds of plant fungi which means that these functionalized tetracyclic compounds might be used in the agrochemical field. Abstract A series of trifluoromethyl‐containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin‐fused tetracyclic compounds have been prepared using copper‐catalyzed cascade reaction of benzene‐tethered 1,7‐enynes. A study of the mechanism indicated that radical trifluoromethylation and sequential 6‐exo‐dig / 5‐endo‐trig bicyclization processes were involved in this protocol. Moreover, some selected products showed certain fungicidal activities against 14 kinds of plant fungi which means that these functionalized tetracyclic compounds might be used in the agrochemical field. magnified image A series of trifluoromethyl-containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin-fused tetracyclic compounds have been prepared using copper-catalyzed cascade reaction of benzene-tethered 1,7-enynes. A study of the mechanism indicated that radical trifluoromethylation and sequential 6-exo-dig/5-endo-trig bicyclization processes were involved in this protocol. More-over, some selected products showed certain fungicidal activities against 14 kinds of plant fungi which means that these functionalized tetracyclic compounds might be used in the agrochemical field. |
| Author | Song, Haibin Wang, Qiang Song, Hongjian Liu, Yuxiu Wang, Qingmin |
| Author_xml | – sequence: 1 givenname: Qiang surname: Wang fullname: Wang, Qiang organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, 300071, Tianjin, People's Republic of China – sequence: 2 givenname: Hongjian surname: Song fullname: Song, Hongjian organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, 300071, Tianjin, People's Republic of China – sequence: 3 givenname: Yuxiu surname: Liu fullname: Liu, Yuxiu organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, 300071, Tianjin, People's Republic of China – sequence: 4 givenname: Haibin surname: Song fullname: Song, Haibin organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, 300071, Tianjin, People's Republic of China – sequence: 5 givenname: Qingmin surname: Wang fullname: Wang, Qingmin email: wangqm@nankai.edu.cn organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, 300071, Tianjin, People's Republic of China |
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| Keywords | fungicidal activity CARBOCYCLIZATION radical cascade reaction BOND FORMATION fused polycycles ALKENES ARYLTRIFLUOROMETHYLATION DEAROMATIZATION ACCESS LIGHT-INDUCED TRIFLUOROMETHYLATION CONSTRUCTION FLUORINE trifluoromethylation CYCLIZATION 1,N-ENYNES |
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| Snippet | A series of trifluoromethyl‐containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin‐fused tetracyclic compounds have been prepared using... A series of trifluoromethyl-containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin-fused tetracyclic compounds have been prepared using... Abstract A series of trifluoromethyl‐containing heterocycles, like indene and dihydroquinolinone or dihydrocoumarin‐fused tetracyclic compounds have been... |
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| SubjectTerms | Agricultural chemicals Catalysis Chemistry Chemistry, Applied Chemistry, Organic Fungi fungicidal activity Fungicides fused polycycles Indene Organic chemistry Physical Sciences radical cascade reaction Radicals Science & Technology Synthesis (chemistry) trifluoromethylation |
| Title | Copper-Catalyzed Trifluoromethylation and Bicyclizations of 1,7-Enynes Leading to Fused Polycycles |
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