Concise Report
Photocatalyzed Annulation-Biselenylation of Enynone with Diarylselenides toward Biselenium-Substituted 1-Indanones under Metal- and Photosensitizer-Free Conditions
Hang-Dong Zuo,
Hua-Feng Yan,
Yu-Ting Wang,
Sheng-Hu Yan,
Cheng Guo,
Yue Zhang,
Jia-Yin Wang,
Corresponding Author
Hang-Dong Zuo
School of Safety Science and Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorHua-Feng Yan
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, Jiangsu, 211816 China
Search for more papers by this authorYu-Ting Wang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorCorresponding Author
Sheng-Hu Yan
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorCheng Guo
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, Jiangsu, 211816 China
Search for more papers by this authorYue Zhang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorCorresponding Author
Jia-Yin Wang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorHang-Dong Zuo,
Hua-Feng Yan,
Yu-Ting Wang,
Sheng-Hu Yan,
Cheng Guo,
Yue Zhang,
Jia-Yin Wang,
Corresponding Author
Hang-Dong Zuo
School of Safety Science and Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorHua-Feng Yan
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, Jiangsu, 211816 China
Search for more papers by this authorYu-Ting Wang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorCorresponding Author
Sheng-Hu Yan
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorCheng Guo
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, Jiangsu, 211816 China
Search for more papers by this authorYue Zhang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorCorresponding Author
Jia-Yin Wang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorFirst published: 17 April 2025
Comprehensive Summary
A practical photocatalytic annulation-biselenylation strategy has been developed for the efficient synthesis of biselenium-substituted 1-indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z/E ratio) by employing enynones and diaryl selenides as starting materials under photosensitizer-free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5-exo-dig cyclization, and radical capture, enabling sequential formation of multiple bonds, such as C(sp3)-Se, C(sp3)-C(sp2), and C(sp2)-Se bonds, to rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility and excellent tolerability towards various functional groups. It is further characterized by its remarkable efficiency in creating chemical bonds and achieving high atomic utilization of 100%.
Supporting Information
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Appendix S1: Supporting Information |
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