Continuous-flow catalytic deuterodehalogenation carried out in propylene carbonate

A selective continuous-flow (CF) deuterodehalogenation approach is described performed in propylene carbonate, which is considered as one of the greenest solvents. Various CF technologies are known for hydrodehalogenation reactions; however, they are not directly transferable for deuteration transfo...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2019, Vol.21 (5), p.956-961
Main Authors: Orsy, György, Fülöp, Ferenc, Mándity, István M
Format: Article
Language:English
Subjects:
Activated carbon
Amides
Bromine
Catalysts
Catalytic converters
Chlorine
Deuteration
Deuterium
Fluorine
Green chemistry
Iodine
NMR
Nuclear magnetic resonance
Optimization
Palladium
Propylene
Substitutes
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Summary:A selective continuous-flow (CF) deuterodehalogenation approach is described performed in propylene carbonate, which is considered as one of the greenest solvents. Various CF technologies are known for hydrodehalogenation reactions; however, they are not directly transferable for deuteration transformations. A novel spherical activated carbon-supported palladium catalyst has been found to be useful for the catalytic deuterodehalogenation of haloarenes. After careful reaction parameter optimization, complete conversion was achieved for bromine- and chlorine-substituted haloarenes. Nonetheless, no deuterium exchange was observed for the fluorine substituent, while iodine-substituted compounds poisoned the catalyst. Importantly, deuterated compounds were obtained with a rate of 3 mg min −1 and the catalyst showed reasonable reusability. Moreover, benzylic amides were also deuterated without any debenzylation side-reaction. Continuous-flow dehalodeuteration of aromatics carried out in propylene carbonate for a liveable future.
ISSN:1463-9262
1463-9270
DOI:10.1039/c8gc03192d