Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations
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Date
2021-01-29
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Journal Article
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yes
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Abstract
Vicinal dibromides and dichlorides are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that are traditionally synthesized using hazardous elemental chlorine and bromine. Meanwhile, the environmental persistence of halogenated pollutants necessitates improved approaches to accelerate their remediation. Here, we introduce an electrochemically assisted shuttle (e-shuttle) paradigm for the facile and scalable interconversion of alkenes and vicinal dihalides, a class of reactions that can be used both to synthesize useful dihalogenated molecules from simple alkenes and to recycle waste material through retro-dihalogenation. The reaction is demonstrated using 1,2-dibromoethane, as well as 1,1,1,2-tetrachloroethane or 1,2-dichloroethane, to dibrominate or dichlorinate, respectively, a wide range of alkenes in a simple setup with inexpensive graphite electrodes. Conversely, the hexachlorinated persistent pollutant lindane could be fully dechlorinated to benzene in soil samples using simple alkene acceptors.
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published
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Science
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371 (6528)
Pages / Article No.
507 - 514
Publisher
AAAS
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Organisational unit
09634 - Morandi, Bill / Morandi, Bill
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757608 - Shuttle Catalysis for Reversible Molecular Construction (EC)
886102 - Elemental Halogen-Free Reversible Construction and Deconstruction of 1,2- Dihalides via Shuttle Catalysis (EC)
886102 - Elemental Halogen-Free Reversible Construction and Deconstruction of 1,2- Dihalides via Shuttle Catalysis (EC)