Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings
Polysulfide anions are endowed with unique redox properties, attracting considerable attentions for their applications in alkali metals-sulfur batteries. However, the employment of these anionic species in redox catalysis for small molecule synthesis remains underdeveloped due to their moderate-poor...
| Main Authors: | , , , , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/154831 |
| _version_ | 1826120851854983168 |
|---|---|
| author | Li, Haoyu Tang, Xinxin Pang, Jia Hao Wu, Xiangyang Yeow, Edwin Kok Lee Wu, Jie Chiba, Shunsuke |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Li, Haoyu Tang, Xinxin Pang, Jia Hao Wu, Xiangyang Yeow, Edwin Kok Lee Wu, Jie Chiba, Shunsuke |
| author_sort | Li, Haoyu |
| collection | NTU |
| description | Polysulfide anions are endowed with unique redox properties, attracting considerable attentions for their applications in alkali metals-sulfur batteries. However, the employment of these anionic species in redox catalysis for small molecule synthesis remains underdeveloped due to their moderate-poor electrochemical potential in the ground state, whereas some of them are characterized by photoabsorptions in visible spectral regions. Herein, we disclose the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. The reaction design enables single-electron reduction of aryl halides upon the photoexcitation of tetrasulfide dianions (S42-). The resulting aryl radicals are engaged in (hetero)biaryl cross-coupling, borylation, and hydrogenation in a redox catalytic regime involving S4• -/S42- and S3• -/S32- redox couples. |
| first_indexed | 2024-10-01T05:23:31Z |
| format | Journal Article |
| id | ntu-10356/154831 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:23:31Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1548312023-02-28T19:58:36Z Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings Li, Haoyu Tang, Xinxin Pang, Jia Hao Wu, Xiangyang Yeow, Edwin Kok Lee Wu, Jie Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Redox Reactions Anions Polysulfide anions are endowed with unique redox properties, attracting considerable attentions for their applications in alkali metals-sulfur batteries. However, the employment of these anionic species in redox catalysis for small molecule synthesis remains underdeveloped due to their moderate-poor electrochemical potential in the ground state, whereas some of them are characterized by photoabsorptions in visible spectral regions. Herein, we disclose the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. The reaction design enables single-electron reduction of aryl halides upon the photoexcitation of tetrasulfide dianions (S42-). The resulting aryl radicals are engaged in (hetero)biaryl cross-coupling, borylation, and hydrogenation in a redox catalytic regime involving S4• -/S42- and S3• -/S32- redox couples. Agency for Science, Technology and Research (A*STAR) Accepted version Financial support was provided by Pharma Innovation Programme Singapore (A*STAR, SERC A19B3a0014). 2022-01-13T05:58:44Z 2022-01-13T05:58:44Z 2021 Journal Article Li, H., Tang, X., Pang, J. H., Wu, X., Yeow, E. K. L., Wu, J. & Chiba, S. (2021). Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings. Journal of the American Chemical Society, 143(1), 481-487. https://dx.doi.org/10.1021/jacs.0c11968 0002-7863 https://hdl.handle.net/10356/154831 10.1021/jacs.0c11968 33356206 2-s2.0-85099106598 1 143 481 487 en SERC A19B3a0014 Journal of the American Chemical Society This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.0c11968. application/pdf |
| spellingShingle | Science::Chemistry Redox Reactions Anions Li, Haoyu Tang, Xinxin Pang, Jia Hao Wu, Xiangyang Yeow, Edwin Kok Lee Wu, Jie Chiba, Shunsuke Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings |
| title | Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings |
| title_full | Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings |
| title_fullStr | Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings |
| title_full_unstemmed | Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings |
| title_short | Polysulfide anions as visible light photoredox catalysts for aryl cross-couplings |
| title_sort | polysulfide anions as visible light photoredox catalysts for aryl cross couplings |
| topic | Science::Chemistry Redox Reactions Anions |
| url | https://hdl.handle.net/10356/154831 |
| work_keys_str_mv | AT lihaoyu polysulfideanionsasvisiblelightphotoredoxcatalystsforarylcrosscouplings AT tangxinxin polysulfideanionsasvisiblelightphotoredoxcatalystsforarylcrosscouplings AT pangjiahao polysulfideanionsasvisiblelightphotoredoxcatalystsforarylcrosscouplings AT wuxiangyang polysulfideanionsasvisiblelightphotoredoxcatalystsforarylcrosscouplings AT yeowedwinkoklee polysulfideanionsasvisiblelightphotoredoxcatalystsforarylcrosscouplings AT wujie polysulfideanionsasvisiblelightphotoredoxcatalystsforarylcrosscouplings AT chibashunsuke polysulfideanionsasvisiblelightphotoredoxcatalystsforarylcrosscouplings |