Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 26, Pages 6781-6785Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201403442
Keywords
dynamic covalent bonds; selenium; supramolecular chemistry
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Funding
- National Basic Research Program of China [2013CB834502]
- Foundation for Innovative Research Groups of the National Natural Science Foundation of China [21121004]
- Tsinghua University Initiative Scientific Research Program [2012Z02131]
- NSFC-DFG joint grant [TRR 61]
- Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions
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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.
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