Copper-catalysed low-temperature water–gas shift reaction for selective deuteration of aryl halides

Abstract

The introduction of deuterium atoms into organic compounds is of importance for basic chemistry, material sciences, and the development of drugs in the pharmaceutical industry, specifically for identification and quantification...

Regioselective Deuteration of Arenes Enabled by Simple Heterogeneous Palladium Catalysis

“…Although recent significant homogeneous palladium-catalytic platforms were well developed for various functionalizations of aryl thianthrenium salts, − many nonnegligible limitations involving high loading of the catalyst, worse performance in separation, and recyclability of the catalyst from the catalytic system would appear to suppress the practical application, especially for the large-scale industrial processes. With the development of sustainable chemistry, some heterogeneous palladium-catalyzed systems have already been developed. − However, the heterogeneous catalytic system for the formation of the C­(sp 2 )–D bond has rarely been reported . Therefore, it is desirable to develop some highly efficient heterogeneous catalytic platforms for the synthesis of deuterium-labeled molecules.…”

“…57−62 However, the heterogeneous catalytic system for the formation of the C(sp 2 )−D bond has rarely been reported. 63 Therefore, it is desirable to develop some highly efficient heterogeneous catalytic platforms for the synthesis of deuterium-labeled molecules. Herein, we reported the first heterogeneous palladium-catalytic deuteration of (hetero) arenes with the only requirement of simple Pd/C catalyst and commercially available DCOONa (Scheme 1e).…”

Modification strategies of heterogeneous catalysts for water–gas shift reactions

“…64 To address this issue, WGSR can be applied as a downstream process (eqn (1)) where CO is converted to CO 2 and H 2 , thus removing carbon monoxide from syngas to obtain high-purity hydrogen and alleviating the release of toxic gases into the atmospheres. 65–76 Considering the exothermic nature, lower temperatures are conducive to higher carbon monoxide conversion; however, high temperatures will increase the reaction rate. Therefore, in commercial applications, the process is carried out in two steps (high-temperature reaction followed by low-temperature conversion) to achieve the purity level required for various industrial applications.…”

Coupling photocatalytic overall water splitting with hydrogenation of organic molecules: a strategy for using water as a hydrogen source and an electron donor to enable hydrogenation

“…37–44 As a result, much attention has been devoted to the deuteration of aromatic rings. 37–44 One of the most effective strategies is the deuteration of aryl halides using DMSO-D 6 , 45 CD 3 OD, 46 DCOONa, 47 THF-d 8 , 48 CH 3 OD 49 and D 2 O 50–54 as deuterium sources (Scheme 1b), among which D 2 O is undoubtedly the most attractive deuteration reagent from the perspective of safety, cost and handling. However, those methods for the deuteration of aryl halides with D 2 O suffer from an expense of polluting reductants such as sodium formate, triethanolamine, sodium sulfite and (Bu 3 Sn) 2 .…”

“…However, those methods for the deuteration of aryl halides with D 2 O suffer from an expense of polluting reductants such as sodium formate, triethanolamine, sodium sulfite and (Bu 3 Sn) 2 . [50][51][52][53][54] Thus we applied our strategy to the deuteration of aryl halides with D 2 O to avoid using those pollutive reductants, which provides an effective and controllable method for synthesizing high value-added deuterated aromatic compounds (Scheme 1c), and the results are reported herein.…”