Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors
The development of suitable electron donors is critical to single-electron-transfer (SET) processes. The use of heteroatom-centered anions as super-electron-donors (SEDs) for direct SET reactions has rarely been studied. Here we show that heteroatom anions can be applied as SEDs to initiate radical...
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sg-ntu-dr.10356-1729942024-03-20T01:37:46Z Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors Jiang, Shichun Wang, Wei Mou, Chengli Zou, Juan Jin, Zhichao Hao, Gefei Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Science::Chemistry Tetrahydrofuran Benzofuran Derivative The development of suitable electron donors is critical to single-electron-transfer (SET) processes. The use of heteroatom-centered anions as super-electron-donors (SEDs) for direct SET reactions has rarely been studied. Here we show that heteroatom anions can be applied as SEDs to initiate radical reactions for facile synthesis of 3-substituted benzofurans. Phosphines, thiols and anilines bearing different substitution patterns work well in this inter-molecular radical coupling reaction and the 3-functionalized benzofuran products bearing heteroatomic functionalities are given in moderate to excellent yields. The reaction mechanism is elucidated via control experiments and computational methods. The afforded products show promising applications in both organic synthesis and pesticide development. Ministry of Education (MOE) National Research Foundation (NRF) Published version We acknowledge financial support from the National Key Research and Development Program of China (2022YFD1700300, Z.J.). National Natural Science Foundation of China [(21961006, Z.J.), (32172459, Z.J.), (22371057, Z.J.), (22071036, Y.R.C), (21732002, Y.R.C.)]. Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY number (2020)004, Y.R.C.]. The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649, Y.R.C.). Science and Technology Department of Guizhou Province (Qiankehejichu-ZK[2021]Key033, Z.J.). Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023, Y.R.C.) at Guizhou University. Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06, Y.R.C.) and Competitive Research Program (NRF-CRP22-2019-0002, Y.R.C.). Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG7/20, RG5/19, Y.R.C.), MOE AcRF Tier 2 (MOE2019-T2-2-117, Y.R.C.), and MOE AcRF Tier 3 Award (MOE2018-T3-1-003, Y.R.C.). 2024-01-08T05:27:12Z 2024-01-08T05:27:12Z 2023 Journal Article Jiang, S., Wang, W., Mou, C., Zou, J., Jin, Z., Hao, G. & Chi, R. Y. (2023). Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors. Nature Communications, 14(1), 1-12. https://dx.doi.org/10.1038/s41467-023-43198-y 2041-1723 https://hdl.handle.net/10356/172994 10.1038/s41467-023-43198-y 14 2-s2.0-85176575293 1 14 7381 en NRF-NRFI2016-06 NRF-CRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 MOE2018-T3-1-003 Nature Communications © 2023 The Author(s). Open Access. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/ licenses/by/4.0/. application/pdf |
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Science::Chemistry Tetrahydrofuran Benzofuran Derivative |
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Science::Chemistry Tetrahydrofuran Benzofuran Derivative Jiang, Shichun Wang, Wei Mou, Chengli Zou, Juan Jin, Zhichao Hao, Gefei Chi, Robin Yonggui Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors |
| description |
The development of suitable electron donors is critical to single-electron-transfer (SET) processes. The use of heteroatom-centered anions as super-electron-donors (SEDs) for direct SET reactions has rarely been studied. Here we show that heteroatom anions can be applied as SEDs to initiate radical reactions for facile synthesis of 3-substituted benzofurans. Phosphines, thiols and anilines bearing different substitution patterns work well in this inter-molecular radical coupling reaction and the 3-functionalized benzofuran products bearing heteroatomic functionalities are given in moderate to excellent yields. The reaction mechanism is elucidated via control experiments and computational methods. The afforded products show promising applications in both organic synthesis and pesticide development. |
| author2 |
School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet |
School of Chemistry, Chemical Engineering and Biotechnology Jiang, Shichun Wang, Wei Mou, Chengli Zou, Juan Jin, Zhichao Hao, Gefei Chi, Robin Yonggui |
| format |
Article |
| author |
Jiang, Shichun Wang, Wei Mou, Chengli Zou, Juan Jin, Zhichao Hao, Gefei Chi, Robin Yonggui |
| author_sort |
Jiang, Shichun |
| title |
Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors |
| title_short |
Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors |
| title_full |
Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors |
| title_fullStr |
Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors |
| title_full_unstemmed |
Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors |
| title_sort |
facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors |
| publishDate |
2024 |
| url |
https://hdl.handle.net/10356/172994 |
| _version_ |
1794549393237475328 |