5284-44-6

Usage

Uses

Used in Research and Development:
TRANS-STILBENE-ALPHA,ALPHA'-D2 is used as a research compound for studying the properties and behavior of stilbene and its derivatives. The incorporation of deuterium in the molecule allows researchers to observe the effects of isotopic substitution on the compound's chemical and physical characteristics.
Used in Pharmaceutical Industry:
TRANS-STILBENE-ALPHA,ALPHA'-D2 is used as a labeled compound in the pharmaceutical industry for the development and testing of new drugs. The isotopically labeled compound can be used to track the distribution, metabolism, and excretion of the drug in the body, providing valuable information for drug design and optimization.
Used in Chemical Synthesis:
In the field of chemical synthesis, TRANS-STILBENE-ALPHA,ALPHA'-D2 can be used as a starting material or an intermediate for the synthesis of other deuterated compounds. The presence of deuterium in the molecule can influence the reaction rates and selectivity, making it a useful tool for studying reaction mechanisms and developing new synthetic routes.
Used in Analytical Chemistry:
TRANS-STILBENE-ALPHA,ALPHA'-D2 is used as a reference material in analytical chemistry for the calibration of instruments and the development of new analytical methods. The isotopically labeled compound can be used to improve the accuracy and precision of measurements, particularly in techniques such as mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy.
Used in Material Science:
In material science, TRANS-STILBENE-ALPHA,ALPHA'-D2 can be used to study the properties of deuterated materials and their potential applications. The incorporation of deuterium in the compound can lead to changes in the material's mechanical, thermal, and electronic properties, which can be of interest for the development of new materials with specific characteristics.

Upstream product

• 3947-91-9 (Z)-1,2-dideuterio-1,2-diphenyl-ethene 
• 501-65-5 diphenyl acetylene 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 98-80-6 phenylboronic acid 
• 811-98-3 d⁽⁴⁾-methanol 
• 42463-63-8 benzyl alcohol-α,α,hydroxy-d3 
• 140-29-4 phenylacetonitrile 
• 15951-99-2 1,2-dichloro-1,2-diphenylethane 

Downstream Products

• 3947-91-9 (Z)-1,2-dideuterio-1,2-diphenyl-ethene 
• 66252-27-5 1,2-diphenyl[1,2-D₂]ethane 
• 36239-19-7 <1,2-2H2>-1,2-diphenyl-1,2-ethanediol 
• 143715-90-6 2-(hydroxy-d)-1,2-diphenylethan-1-one-2-d 

Relevant academic research and scientific papers

Ruthenium-Catalyzed E-Selective Partial Hydrogenation of Alkynes under Transfer-Hydrogenation Conditions using Paraformaldehyde as Hydrogen Source

E-alkenes were synthesized with up to 100 % E/Z selectivity via ruthenium-catalyzed partial hydrogenation of different aliphatic and aromatic alkynes under transfer-hydrogenation conditions. Paraformaldehyde as a safe, cheap and easily available solid hydrogen carrier was used for the first time as hydrogen source in the presence of water for transfer-hydrogenation of alkynes. Optimization reactions showed the best results for the commercially available binuclear [Ru(p-cymene)Cl2]2 complex as pre-catalyst in combination with 2,2-bis(diphenylphosphino)-1,1-binaphthyl (BINAP) as ligand (1 : 1 ratio per Ru monomer to ligand). Mechanistic investigations showed that the origin of E-selectivity in this reaction is the fast Z to E isomerization of the formed alkenes. Mild reaction conditions plus the use of cheap, easily available and safe materials as well as simple setup and inexpensive catalyst turn this protocol into a feasible and promising stereo complementary procedure to the well-known Z-selective Lindlar reduction in late-stage syntheses. This procedure can also be used for the production of deuterated alkenes simply using d2-paraformaldehyde and D2O mixtures.

Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen-Deuterium Exchange Reactions

Herein we have developed a reversible hydrogen-deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of compatibility of functional groups was achieved.

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

A Bidentate Ru(II)-NC Complex as a Catalyst for Semihydrogenation of Alkynes to (E)-Alkenes with Ethanol

Four Ru(II)-NC complexes were tested as catalysts for semihydrogenation of internal alkynes to (E)-alkenes with ethanol, and the complex {(C5H4N)(C6H4)}RuCl(CO)(PPh3)2 (1a) showed the highest activity. The reactions proceeded well with 1 mol % catalyst loading and 0.1 equiv of t-BuONa at 110 °C for 1 h, and 32 alkenes were synthesized with excellent E:Z selectivity. This is the first ruthenium-catalyzed semihydrogenation of internal alkynes to (E)-alkenes using ethanol as the hydrogen donor.

Rare-Earth Supported Nickel Catalysts for Alkyne Semihydrogenation: Chemo- And Regioselectivity Impacted by the Lewis Acidity and Size of the Support

Bimetallic catalysts of nickel(0) with a trivalent rare-earth ion or Ga(III), NiML3 (where L is [iPr2PCH2NPh]-, and M is Sc, Y, La, Lu, or Ga), were investigated for the selective hydrogenation of diphenylacetylene (DPA) to (E)-stilbene. Each bimetallic complex features a relatively short Ni-M bond length, ranging from 2.3395(8) ? (Ni-Ga) to 2.5732(4) ? (Ni-La). The anodic peak potentials of the NiML3 complexes vary from -0.48 V to -1.23 V, where the potentials are negatively correlated with the Lewis acidity of the M(III) ion. Three catalysts, Ni-Y, Ni-Lu, and Ni-Ga, showed nearly quantitative conversions in the semihydrogenation of DPA, with NiYL3 giving the highest selectivity for (E)-stilbene. Initial rate studies were performed on the two tandem catalytic reactions: DPA hydrogenation and (Z)-stilbene isomerization. The catalytic activity in DPA hydrogenation follows the order Ni-Ga > Ni-La > Ni-Y > Ni-Lu > Ni-Sc. The ranking of catalysts by (Z)-stilbene isomerization initial rates is Ni-Ga ? Ni-Sc > Ni-Lu > Ni-Y > Ni-La. In operando 31P and 1H NMR studies revealed that in the presence of DPA, the Ni bimetallic complexes supported by Y, Lu, and La form the Ni(η2-alkyne) intermediate, (η2-PhCCPh)Ni(iPr2PCH2NPh)2M(κ2-iPr2PCH2NPh). In contrast, the Ni-Ga resting state is the Ni(η2-H2) species, and Ni-Sc showed no detectable binding of either substrate. Hence, the mechanism of Ni-catalyzed diphenylacetylene semihydrogenation adheres to two different kinetics: an autotandem pathway (Ni-Ga, Ni-Sc) versus temporally separated tandem reactions (Ni-Y, Ni-Lu, Ni-La). Collectively, the experimental results demonstrate that modulating a base-metal center via a covalently appended Lewis acidic support is viable for promoting selective alkyne semihydrogenation.

Mild, Selective Ru-Catalyzed Deuteration Using D2O as a Deuterium Source

A method for the selective deuteration of polyfunctional organic molecules using catalytic amounts of [RuCl2(PPh3)3] and D2O as a deuterium source is presented. Through variation of additives like CuI, KOH, and various amounts of zinc powder, orthogonal chemoselectivities in the deuteration process are observed. Mechanistic investigation indicates the presence of different, defined Ru-complexes under the given specific conditions.

Xanthate-mediated synthesis of (E)-alkenes by semi-hydrogenation of alkynes using water as the hydrogen donor

Semi-hydrogenation of alkynes is one of the most widely used methods for obtaining alkenes in laboratory preparation and in industry. Transition metal catalysts have been extensively studied for this transformation, but the tolerance of functional groups, such as pyridine,-OH,-NH2,-Bpin, and halides, and the toxicity of the trace amount of transition metal catalysts are still highly challenging. In this study, we report a general and robust strategy to achieve the semi-hydrogenation of alkynes using inexpensive and commercially available xanthate as the mediator. Mechanism studies support a non-radical process and H2O acts as the hydrogen donor.

Water as a Hydrogenating Agent: Stereodivergent Pd-Catalyzed Semihydrogenation of Alkynes

Palladium-catalyzed transfer semihydrogenation of alkynes using H2O as the hydrogen source and Mn as the reducing reagent is developed, affording cis- and trans-alkenes selectively under mild conditions. In addition, this method provides an efficient way to access various cis-1,2-dideuterioalkenes and trans-1,2-dideuterioalkenes by using D2O instead of H2O.

Stereodivergent Alkyne Reduction by using Water as the Hydrogen Source

A homogeneous Pd-catalyzed stereodivergent reduction of alkynes to Z and E alkenes by using H2O as the H2 source is presented. Mediated by a diboron reagent, the transfer hydrogenation has been accomplished to yield the desired geometrical isomer by rational ligand selection. The switchable stereoselectivity achieved using simple phosphine ligands is generally excellent. D2O has also been used as a D2 source for synthesizing the corresponding deuterated olefins. Supported by a gram-scale synthesis, the reaction can easily be scaled up making it an efficient way to prepare alkenes commercially as well. Mechanistic studies suggest formation of H?PdL2?OAc as the crucial step leading to the presence of two pathways involving H?Pd?B(OR)2 and molecular H2 as active intermediates.

Ru-Catalyzed Transfer Hydrogenation of Nitriles, Aromatics, Olefins, Alkynes and Esters

This paper reports the preparation of new ruthenium(II) complexes supported by a pyrazole-phosphine ligand and their application to transfer hydrogenation of various substrates. These Ru complexes were found to be efficient catalysts for the reduction of nitriles and olefins. Heterocyclic compounds undergo transfer hydrogenation with good to moderate yields, affording examples of unusual hydrogenation of all-carbon-rings. Internal alkynes with bulky substituents show selective reduction to olefins with the unusual E–selectivity. Esters with strong electron-withdrawing groups can be reduced to the corresponding alcohols, if ethanol is used as the solvent. Possible mechanisms of hydrogenation and olefin isomerization are suggested on the basis of kinetic studies and labelling experiments.