Dynamic Diselenide Bonds: Exchange Reaction Induced by Visible Light without Catalysis
Dynamic covalent bonds are extensively employed in dynamic combinatorial chemistry. The metathesis reaction of disulfide bonds is widely used, but requires catalysis or irradiation with ultraviolet (UV) light. It was found that diselenide bonds are dynamic covalent bonds and undergo dynamic exchange...
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| Published in: | Angewandte Chemie International Edition Vol. 53; no. 26; pp. 6781 - 6785 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Weinheim
WILEY-VCH Verlag
23-06-2014
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
| Edition: | International ed. in English |
| Subjects: | |
| Online Access: | Get full text |
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| Summary: | Dynamic covalent bonds are extensively employed in dynamic combinatorial chemistry. The metathesis reaction of disulfide bonds is widely used, but requires catalysis or irradiation with ultraviolet (UV) light. It was found that diselenide bonds are dynamic covalent bonds and undergo dynamic exchange reactions under mild conditions for diselenide metathesis. This reaction is induced by irradiation with visible light and stops in the dark. The exchange is assumed to proceed through a radical mechanism, and experiments with 2,2,6,6‐tetramethylpiperidin‐1‐yloxyl (TEMPO) support this assumption. Furthermore, the reaction can be conducted in different solvents, including protic solvents. Diselenide metathesis can also be used to synthesize diselenide‐containing asymmetric block copolymers. This work thus entails the use of diselenide bonds as dynamic covalent bonds, the development of a dynamic exchange reaction under mild conditions, and an extension of selenium‐related dynamic chemistry.
Diselenide bonds are dynamic covalent bonds. Their metathesis can be induced by irradiation with visible light and likely proceeds through a radical mechanism, as the exchange reaction between two different diselenides was suppressed by the addition of the radical scavenger 2,2,6,6‐tetramethylpiperidine N‐oxide (TEMPO). |
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| Bibliography: | The Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions Tsinghua University Initiative Scientific Research Program - No. 2012Z02131 NSFC-DFG - No. TRR 61 This work was financially supported by the National Basic Research Program of China (2013CB834502), the Foundation for Innovative Research Groups of the National Natural Science Foundation of China (21121004), Tsinghua University Initiative Scientific Research Program (2012Z02131), the NSFC-DFG joint grant (TRR 61), and The Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions. We acknowledge Prof. Xi Zhang and Prof. Meixiang Wang (Tsinghua University) for their stimulating suggestions, and Prof. Hideyuki Otsuka (Kyushu University), Dr. Lei Tao, and Dr. Haijun Yang (Tsinghua University) for constructive discussions. istex:D5C25BBE33CCEACF7F1B92FCDA97BA6F435D81D2 ark:/67375/WNG-M60FB68K-M ArticleID:ANIE201403442 National Natural Science Foundation of China - No. 21121004 National Basic Research Program of China - No. 2013CB834502 This work was financially supported by the National Basic Research Program of China (2013CB834502), the Foundation for Innovative Research Groups of the National Natural Science Foundation of China (21121004), Tsinghua University Initiative Scientific Research Program (2012Z02131), the NSFC‐DFG joint grant (TRR 61), and The Importation and Development of High‐Caliber Talents Project of Beijing Municipal Institutions. We acknowledge Prof. Xi Zhang and Prof. Meixiang Wang (Tsinghua University) for their stimulating suggestions, and Prof. Hideyuki Otsuka (Kyushu University), Dr. Lei Tao, and Dr. Haijun Yang (Tsinghua University) for constructive discussions. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 1433-7851 1521-3773 |
| DOI: | 10.1002/anie.201403442 |