Scalable and selective deuteration of (hetero)arenes

Isotope labelling, particularly deuteration, is an important tool for the development of new drugs, specifically for identification and quantification of metabolites. For this purpose, many efficient methodologies have been developed that allow for the small-scale synthesis of selectively deuterated compounds. Due to the development of deuterated compounds as active drug ingredients, there is a growing interest in scalable methods for deuteration. The development of methodologies for large-scale deuterium labelling in industrial settings requires technologies that are reliable, robust and scalable. Here we show that a nanostructured iron catalyst, prepared by combining cellulose with abundant iron salts, permits the selective deuteration of (hetero)arenes including anilines, phenols, indoles and other heterocycles, using inexpensive D2O under hydrogen pressure. This methodology represents an easily scalable deuteration (demonstrated by the synthesis of deuterium-containing products on the kilogram scale) and the air- and water-stable catalyst enables efficient labelling in a straightforward manner with high quality control.

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

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...

Transition-metal-free Decarbonylative Alkylation of N-Aryl a-Hydroxy Amides via Triple C–C Bond Cleavages and Their Selective Deuteration

We disclose a transition-metal-free decarbonylative alkylation reaction for the synthesis of N-aryl a-hydroxy amides via precise cleavages and reorganizations of three C–C s bonds. For the first time, the medium-sized...

Site-selective deuteration of diaryl alcohols by D2O via quantum dots photocatalysis

Owing to high synthetic value of deuteration in pharmaceutical industry, we describe herein a range of aromatic ketones being converted to deuterium-labeled products in good to excellent yields. Efficient and...

Formyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis

Formyl-selective deuteration of aldehydes with D2O mediated by the synergistic combination of light-driven, polyoxometalate-facilitated HAT and thiol catalysis is reported.

Mild and Green Protocol for Selective Deuteration of Quercetin-3-ORutinoside (Rutin) Under Aqueous Basic Conditions

A convenient and cost-effective method for selective deuteration of rutin using biologically compatible bases and D2O both as a deuterium source and a solvent is herein reported. The protocol is benign and inexpensive affording good results in very mild conditions allowing to reduce the required amount of deuterium oxide. The position of the C-H/C-D exchange and the level of deuteration can be conveniently followed by 1H-NMR.