Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones
A metal-free visible-light-induced synthesis of aza-polycyclic aromatic hydrocarbons via cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole was developed. The reaction was carried out with inactive alkanes and cyclic ethers as alkylation reagents, and phenanthrenequinone (PQ) as...
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KeAi Communications Co. Ltd.
2024-11-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666554923000790 |
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| author | Yanhong Wang Xinlei Zhou Tao Zhang Xinxin Ren Wei Xu Bin Wang Weiwei Jin Yu Xia Chenjiang Liu Yonghong Zhang |
| author_facet | Yanhong Wang Xinlei Zhou Tao Zhang Xinxin Ren Wei Xu Bin Wang Weiwei Jin Yu Xia Chenjiang Liu Yonghong Zhang |
| author_sort | Yanhong Wang |
| collection | DOAJ |
| description | A metal-free visible-light-induced synthesis of aza-polycyclic aromatic hydrocarbons via cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole was developed. The reaction was carried out with inactive alkanes and cyclic ethers as alkylation reagents, and phenanthrenequinone (PQ) as a direct hydrogen-atom transfer (HAT) photocatalyst. The desired products were obtained in moderate to good yields at room temperature under air. |
| format | Article |
| id | doaj-art-b21203011ce64926827b22e4ca9e5e2c |
| institution | Kabale University |
| issn | 2666-5549 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj-art-b21203011ce64926827b22e4ca9e5e2c2024-11-30T07:14:16ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492024-11-0154319323Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-onesYanhong Wang0Xinlei Zhou1Tao Zhang2Xinxin Ren3Wei Xu4Bin Wang5Weiwei Jin6Yu Xia7Chenjiang Liu8Yonghong Zhang9State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, ChinaState Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, ChinaState Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, ChinaState Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, ChinaState Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, ChinaState Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, ChinaState Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, ChinaState Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, ChinaState Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, China; College of Future Technology, Xinjiang University, Urumqi 830017, China; Corresponding author. State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang, 830017, China.State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, China; Corresponding author. State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang, 830017, China.A metal-free visible-light-induced synthesis of aza-polycyclic aromatic hydrocarbons via cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole was developed. The reaction was carried out with inactive alkanes and cyclic ethers as alkylation reagents, and phenanthrenequinone (PQ) as a direct hydrogen-atom transfer (HAT) photocatalyst. The desired products were obtained in moderate to good yields at room temperature under air.http://www.sciencedirect.com/science/article/pii/S2666554923000790Visible light catalysisPhenanthrenequinoneBenzimidazole[2,1-a]isoquinoline-6(5H)-onesRadical cascade reactionsHydrogen atom transfer (HAT) |
| spellingShingle | Yanhong Wang Xinlei Zhou Tao Zhang Xinxin Ren Wei Xu Bin Wang Weiwei Jin Yu Xia Chenjiang Liu Yonghong Zhang Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones Green Synthesis and Catalysis Visible light catalysis Phenanthrenequinone Benzimidazole[2,1-a]isoquinoline-6(5H)-ones Radical cascade reactions Hydrogen atom transfer (HAT) |
| title | Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones |
| title_full | Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones |
| title_fullStr | Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones |
| title_full_unstemmed | Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones |
| title_short | Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones |
| title_sort | visible light induced radical cascade alkylation cyclization of n methacryloyl 2 phenylbenzimidazole access to benzoimidazo 2 1 a isoquinolin 6 5h ones |
| topic | Visible light catalysis Phenanthrenequinone Benzimidazole[2,1-a]isoquinoline-6(5H)-ones Radical cascade reactions Hydrogen atom transfer (HAT) |
| url | http://www.sciencedirect.com/science/article/pii/S2666554923000790 |
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