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Relevant academic research and scientific papers

Borohydride exchange resin as an alternative method for deuterium labelling: selective reduction of aryl bromides

Transition metal-activated borohydride exchange resin and borodeuteride exchange resin have been prepared and used for the selective reductive deuteration of aryl bromides. This methodology, which utilizes deuterated methanol as the primary source of labe

A visible-light-photocatalytic water-splitting strategy for sustainable hydrogenation/deuteration of aryl chlorides

Hydrogenation/deuteration of carbon chloride (C?Cl) bonds is of high significance but remains a remarkable challenge in synthetic chemistry, especially using safe and inexpensive hydrogen donors. In this article, a visible-light-photocatalytic watersplitting hydrogenation technology (WSHT) is proposed to in-situ generate active H-species (i.e., Had) for controllable hydrogenation of aryl chlorides instead of using flammable H2. When applying heavy water-splitting systems, we could selectively install deuterium at the C?Cl position of aryl chlorides under mild conditions for the sustainable synthesis of high-valued added deuterated chemicals. Sub-micrometer Pd nanosheets (Pd NSs) decorated crystallined polymeric carbon nitrides (CPCN) is developed as the bifunctional photocatalyst, whereas Pd NSs not only serve as a cocatalyst of CPCN to generate and stabilize H (D)-species but also play a significant role in the sequential activation and hydrogenation/deuteration of C?Cl bonds. This article highlights a photocatalytic-WSHT for controllable hydrogenation/deuteration of low-cost aryl chlorides, providing a promising way for the photosynthesis of high-valued added chemicals instead of the hydrogen evolution.

Implementing Hydrogen Atom Transfer (HAT) Catalysis for Rapid and Selective Reductive Photoredox Transformations in Continuous Flow

The reductive transformation of aryl halides and carbonyl compounds is a key step in many photoredox transformations. By combining a highly reducing organic photocatalyst with a thiol hydrogen atom transfer (HAT) catalyst, we showcase rapid and highly selective reactions of these synthetically important starting materials in continuous flow. The fast reduction of aryl iodides, bromides and chlorides has been demonstrated with residence times in some cases below one minute. Selectivity between mono- and di-dehalogenation could also be achieved in some cases. Aryl ketones, aldehydes and imines were shown to undergo facile pinacol couplings, and the coupling of an aryl chloride with a styrene was also successful.

Hydro/deutero deamination of arylazo sulfones under metal and (photo)catalyst-free conditions

Hydrodeaminated and monodeuterated aromatics were obtained via a visible-light driven reaction of arylazo sulfones. Deuteration occurs efficiently in deuterated media such as isopropanol-d8 or in THF-d8/water mixtures and exhibits a high tolerance to the nature and the position of the aromatic substituents.

A preparing method of deuterated aromatic compounds

The invention belongs to the field of chemical synthesis, particularly a preparing method of deuterated aromatic compounds. The method includes subjecting an aryl halide, as an initial raw material, to a palladium catalyzed carbon-halogen bond reduction r

A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

Transition metal–catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper’s capacity to broadly facilitate haloarene coupling protocols. Here, we demonstrate that this copper oxidative addition problem can be overcome with an aryl radical–capture mechanism, wherein the aryl radical is generated through a silyl radical halogen abstraction. This strategy was applied to a general trifluoromethylation of aryl bromides through dual copper-photoredox catalysis. Mechanistic studies support the formation of an open-shell aryl species.

Catalytic selective deuteration of halo(hetero)arenes

Deuterium labeled aromatic and heteroaromatic compounds are synthesized in good to excellent yields with >98% deuterium purity via palladium catalyzed deuterodehalogenation reaction using commercially available and inexpensive reagents. Selective deuteration of bromoaniline is also demonstrated without H/D exchange in an amino N-H group.

Efficient Route to Deuterated Aromatics by the Deamination of Anilines

One-step replacement of NH2 groups in ring-substituted anilines by deuterium is reported. Approaches comprising both solid-phase and solution-phase syntheses can be used on a large variety of substrates. The method uses diazotization in a mixture of water and either dichloromethane or chloroform, which serve as a source of hydrogen. This protocol can be used as a general method for fast and easy incorporation of deuterium into an aromatic system using deuterated chloroform.

Selective copper- or silver-catalyzed decarboxylative deuteration of aromatic carboxylic acids

The practical utility of decarboxylative transformations in organic synthesis is discussed, and the decarboxylative deuteration of (hetero)aromatic carboxylic acids is disclosed as a further example. Various monodeuterated arenes were synthesized under mild conditions, in a single step from easily accessible aromatic carboxylic acids and deuterium oxide. Copper catalysts were found to have the widest scope, but silver catalysts are superior for some ortho-substituted benzoates. A few substrates, e.g. quinoline-2-carboxylic acid, decarboxylate even in the absence of a metal catalyst. Georg Thieme Verlag Stuttgart · New York.

CAN-mediated oxidation of electron-deficient aryl and heteroaryl hydrazines and hydrazides

Aryl and heteroaryl hydrazines and hydrazides were successfully oxidised using CAN, deriving dehydrazinated products. The reaction pathway strongly depends on the nature of the substrate, resulting in the formation of hydrocarbons or alkoxy derivatives. When deuterated solvents such as methanol-d4 or acetonitrile-d3 were used, a regiospecific incorporation of deuterium was achieved. Georg Thieme Verlag Stuttgart.