Biaryl cross-coupling enabled by photo-induced electron transfer
We report a protocol for aryl cross-coupling of electron-deficient aryl halides with electron-rich (hetero)arenes that is driven solely by violet light. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)aren...
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sg-ntu-dr.10356-1548362023-02-28T19:21:22Z Biaryl cross-coupling enabled by photo-induced electron transfer Hayashi, Hirohito Wang, Bin Wu, Xiangyang Teo, Shi Jie Kaga, Atsushi Watanabe, Kohei Takita, Ryo Yeow, Edwin Kok Lee Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Aryl Radicals Anion Radicals We report a protocol for aryl cross-coupling of electron-deficient aryl halides with electron-rich (hetero)arenes that is driven solely by violet light. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)arenes to form a pair of aryl anion and cation radicals. The resulting aryl anion radicals of aryl halides undergo mesolysis of the carbon-halogen bond to generate aryl radicals, that are coupled most likely with aryl cation radicals to afford functionalized biaryls. (Figure presented.). Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by funding from Nanyang Technological University (for S.C. and E.K.L.Y), the Singapore Ministry of Education (Academic Research Fund Tier 1: RG2/ 18 for S.C. and RG6/18 for E.K.L.Y), JSPS Grant-in-Aid for Scientific Research (C) (19K0662) (for R.T.) and Uehara Memorial Foundation (for R.T.). The computations were performed using Research Center for Computational Science at Okazaki, Japan. 2022-01-13T07:44:38Z 2022-01-13T07:44:38Z 2020 Journal Article Hayashi, H., Wang, B., Wu, X., Teo, S. J., Kaga, A., Watanabe, K., Takita, R., Yeow, E. K. L. & Chiba, S. (2020). Biaryl cross-coupling enabled by photo-induced electron transfer. Advanced Synthesis & Catalysis, 362(11), 2223-2231. https://dx.doi.org/10.1002/adsc.201901601 1615-4150 https://hdl.handle.net/10356/154836 10.1002/adsc.201901601 2-s2.0-85083845486 11 362 2223 2231 en RG2/18 RG6/18 Advanced Synthesis & Catalysis This is the peer reviewed version of the following article: Hayashi, H., Wang, B., Wu, X., Teo, S. J., Kaga, A., Watanabe, K., Takita, R., Yeow, E. K. L. & Chiba, S. (2020). Biaryl cross-coupling enabled by photo-induced electron transfer. Advanced Synthesis & Catalysis, 362(11), 2223-2231, which has been published in final form at https://doi.org/10.1002/adsc.201901601. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf |
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Science::Chemistry Aryl Radicals Anion Radicals Hayashi, Hirohito Wang, Bin Wu, Xiangyang Teo, Shi Jie Kaga, Atsushi Watanabe, Kohei Takita, Ryo Yeow, Edwin Kok Lee Chiba, Shunsuke Biaryl cross-coupling enabled by photo-induced electron transfer |
| description |
We report a protocol for aryl cross-coupling of electron-deficient aryl halides with electron-rich (hetero)arenes that is driven solely by violet light. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)arenes to form a pair of aryl anion and cation radicals. The resulting aryl anion radicals of aryl halides undergo mesolysis of the carbon-halogen bond to generate aryl radicals, that are coupled most likely with aryl cation radicals to afford functionalized biaryls. (Figure presented.). |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Hayashi, Hirohito Wang, Bin Wu, Xiangyang Teo, Shi Jie Kaga, Atsushi Watanabe, Kohei Takita, Ryo Yeow, Edwin Kok Lee Chiba, Shunsuke |
| format |
Article |
| author |
Hayashi, Hirohito Wang, Bin Wu, Xiangyang Teo, Shi Jie Kaga, Atsushi Watanabe, Kohei Takita, Ryo Yeow, Edwin Kok Lee Chiba, Shunsuke |
| author_sort |
Hayashi, Hirohito |
| title |
Biaryl cross-coupling enabled by photo-induced electron transfer |
| title_short |
Biaryl cross-coupling enabled by photo-induced electron transfer |
| title_full |
Biaryl cross-coupling enabled by photo-induced electron transfer |
| title_fullStr |
Biaryl cross-coupling enabled by photo-induced electron transfer |
| title_full_unstemmed |
Biaryl cross-coupling enabled by photo-induced electron transfer |
| title_sort |
biaryl cross-coupling enabled by photo-induced electron transfer |
| publishDate |
2022 |
| url |
https://hdl.handle.net/10356/154836 |
| _version_ |
1759853916054355968 |