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
Main Authors: Orsy György
Fülöp Ferenc
Mándity István
Format: Article
Published: 2019
Series:GREEN CHEMISTRY 21 No. 5
doi:10.1039/c8gc03192d

mtmt:30638150
Online Access:http://publicatio.bibl.u-szeged.hu/15784
Description
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.
Physical Description:956-961
ISSN:1463-9262