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Issue 5, 2019
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Continuous-flow catalytic deuterodehalogenation carried out in propylene carbonate

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Abstract

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.

Graphical abstract: Continuous-flow catalytic deuterodehalogenation carried out in propylene carbonate

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Supplementary files

Article information


Submitted
11 Oct 2018
Accepted
11 Jan 2019
First published
16 Jan 2019

Green Chem., 2019,21, 956-961
Article type
Communication

Continuous-flow catalytic deuterodehalogenation carried out in propylene carbonate

G. Orsy, F. Fülöp and I. M. Mándity, Green Chem., 2019, 21, 956
DOI: 10.1039/C8GC03192D

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