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Relevant academic research and scientific papers

Combining microwave-enhanced deuteriation reactions with parallel synthesis procedures

The development of combined microwave-enhanced/parallel synthesis procedures and their application to the deuteriation of organic compounds via examples of solid-state hydrogenation is reported. Other labelling procedures, such as solution state catalytic

Chemical-Reductant-Free Electrochemical Deuteration Reaction using Deuterium Oxide

We report a method for the electrochemical deuteration of α,β-unsaturated carbonyl compounds under catalyst- and external-reductant-free conditions, with deuteration rates as high as 99 percent and yields up to 91 percent in 2 h. The use of graphite felt for both the cathode and the anode was key to ensuring chemoselectivity and high deuterium incorporation under neutral conditions without the need for an external reductant. This method has a number of advantages over previously reported deuteration reactions that use stoichiometric metallic reductants. Mechanistic experiments showed that O2 evolution at the anode not only eliminates the need for an external reductant but also regulates the pH of the reaction mixture, keeping it approximately neutral.

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).

Copper-Catalyzed Oxidative Benzylic C(sp3)?H Cyclization for the Synthesis of β-Lactams

β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp3)?H amidation for the synthesis of β-lactams using tBuOOtBu. This method

A selective and cost-effective method for the reductive deuteration of activated alkenes

A new single electron transfer reaction for the reductive deuteration of activated alkenes has been developed for the selective synthesis of α,β-dideuterio compounds. A cheap, stable and commercially-available sodium dispersion with high specific surface

Two-chamber hydrogen generation and application: Access to pressurized deuterium gas

Hydrogen and deuterium gas were produced and directly applied in a two-chamber system. These gaseous reagents were generated by the simple reaction of metallic zinc with HCl in water for H2 and DCl in deuterated water for D2. The setup proved efficient in classical Pd-catalyzed reductions of ketones, alkynes, alkenes, etc. in near-quantitative yields. The method was extended to the synthesis and isotope labeling of quinoline and 1,2,3,4-tetrahydroquinoline derivatives. Finally, CX-546 and Olaparib underwent efficient Ir-catalyzed hydrogen isotope exchange reactions.

A simple, efficient, and selective deuteration via a flow chemistry approach

A simple and efficient deuteration methodology has been established for a wide variety of substrates using a continuous flow hydrogenation reactor. The described procedure is many times faster (1 mg min-1) compared to literature methods and the

Facile and convenient method of deuterium gas generation using a Pd/C-catalyzed H2-D2 exchange reaction and itsapplication to synthesis of deuterium-labeled compounds

The Pd/C-catalyzed H2-D2 exchange reaction using a H2-D2O combination provided a general, efficient and environmentally friendly route for the preparation of deuterium gas (D 2). H2 sealed

Synthesis of different deuterated carboxylic acids from unsaturated acids promoted by samarium diiodide and D2O

An easy, and rapid reduction of the C=C bond of α,β-unsaturated acids by means of samarium diiodide in the presence of D2O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-α,δ-dideuterio-βγ-unsaturated acids are obtained, the new C=C bond being generated with complete diastereoselectivity. When H2O is used instead of D2O, saturated carboxylic acids and (E)-β,γ-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.

New insight into the mechanism of catalytic hydrogenation allows the structure of the key intermediate in asymmetric hydrogenation to be predicted

An approach has been developed to determine the regioselectivity of hydrometalation in homogeneous and heterogeneous hydrogenation of alkenes. By studying the electronic effects on the orientation of hydrometalation it is found with palladium and rhodium that this key step is a two electron process that can occur by two modes (a Pd(δ*+-) H(δ-) or b Pd(δ-)- H(δ+)). This provides valuable information about the structure of the metal-alkyl intermediate and helps rationalise how chiral induction occurs.