Journal
GREEN CHEMISTRY
Volume 21, Issue 5, Pages 956-961Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8gc03192d
Keywords
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Funding
- Hungarian Research Foundation (OTKA) [K 115731]
- [GINOP-2.3.2-15-2016-00014]
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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.
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