22139-13-5

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 588-73-8 (Z)-β-bromostyrene 
• 103-64-0 bromostyrene 
• 811-98-3 d⁽⁴⁾-methanol 
• 100-42-5 styrene 
• 3240-11-7 Phenylacetylene-d1 
• 201230-82-2 carbon monoxide 
• 73183-34-3 bis(pinacol)diborane 
• 4110-77-4 (E)-β-chlorostyrene 
• 42599-24-6 E-styryl iodide 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 536-74-3 phenylacetylene 
• 873-73-4 4-n-chlorophenylacetylene 

Downstream Products

• 77249-39-9 trans-1,1-dibromo-2-phenylcyclopropane-3-d 
• 77249-50-4 cis-1,1-dibromo-2-phenylcyclopropane-3-d 
• 67213-45-0 2-phenylethanol-1,2-d₂ 
• 81541-03-9 2-phenylethyl-1,2-d₂-amine 
• 74498-76-3 C₈H₇⁽²⁾HBrF 
• 927267-87-6 (1R,2R)-1-phenyl-[2-2H₁]ethane-1,2-diol 
• 26631-76-5 2-phenylethyl-1,2-d₂ tosylate 
• 26631-77-6 2-phenylethyl-1,2-d₂-dimethylamine 
• 104960-11-4 2-(p-nitrophenyl)ethyl-1,2-d₂-dimethylamine 
• 104960-08-9 2-phenylethyl-1,2-d₂-trimethylammonium iodide 
• 104960-12-5 2-(p-nitrophenyl)ethyl-1,2-d₂-trimethylammonium iodide 

Relevant academic research and scientific papers

Unexpected CO Dependencies, Catalyst Speciation, and Single Turnover Hydrogenolysis Studies of Hydroformylation via High Pressure NMR Spectroscopy

Rhodium bis(diazaphospholane) (BDP) catalyzed hydroformylation of styrene is sensitive to CO concentration, and drastically different kinetic regimes are affected by modest changes in gas pressure. The Wisconsin High Pressure NMR Reactor (WiHP-NMRR) has e

Biocatalytic Site-Selective Hydrogen Isotope Exchange of Unsaturated Fragments with D2O

Deuterated unsaturated fragments have gained increasing attention because of their roles in understanding reaction mechanisms and pharmaceutical potentials. Due to the difficulties of the existing synthetic methods, it is highly desirable to develop an ef

Visible-Light-Enhanced Cobalt-Catalyzed Hydrogenation: Switchable Catalysis Enabled by Divergence between Thermal and Photochemical Pathways

The catalytic hydrogenation activity of the readily prepared, coordinatively saturated cobalt(I) precatalyst, (R,R)-(iPrDuPhos)Co(CO)2H ((R,R)-iPrDuPhos = (+)-1,2-bis[(2R,5R)-2,5-diisopropylphospholano]benzene), is described. While efficient turnover was observed with a range of alkenes upon heating to 100 °C, the catalytic performance of the cobalt catalyst was markedly enhanced upon irradiation with blue light at 35 °C. This improved reactivity enabled hydrogenation of terminal, di-, and trisubstituted alkenes, alkynes, and carbonyl compounds. A combination of deuterium labeling studies, hydrogenation of alkenes containing radical clocks, and experiments probing relative rates supports a hydrogen atom transfer pathway under thermal conditions that is enabled by a relatively weak cobalt-hydrogen bond of 54 kcal/mol. In contrast, data for the photocatalytic reactions support light-induced dissociation of a carbonyl ligand followed by a coordination-insertion sequence where the product is released by combination of a cobalt alkyl intermediate with the starting hydride, (R,R)-(iPrDuPhos)Co(CO)2H. These results demonstrate the versatility of catalysis with Earth-abundant metals as pathways involving open-versus closed-shell intermediates can be switched by the energy source.

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

Palladium-catalyzed regioselective hydroboration of aryl alkenes with B2pin2

A palladium(ii)-catalyzed hydroboration of aryl alkenes with stable and easy-to-handle (pinacolato)diboron (B2pin2) under mild conditions has been developed. Acetic acid acted as the solvent and the hydrogen source, which has been identified by deuterium experiments. Notably, isomerization-hydroboration of allyl benzene derivatives was observed. As a result, a series of benzyl boronic esters were obtained in moderate to excellent yields with exclusive regioselectivity.

Ligand-Controlled Cobalt-Catalyzed Transfer Hydrogenation of Alkynes: Stereodivergent Synthesis of Z- and E-Alkenes

Herein, we report a novel cobalt-catalyzed stereodivergent transfer hydrogenation of alkynes to Z- and E-alkenes. Effective selectivity control is achieved based on a rational catalyst design. Moreover, this mild system allows for the transfer hydrogenation of alkynes bearing a wide range of functional groups in good yields using catalyst loadings as low as 0.2 mol %. The general applicability of this procedure is highlighted by the synthesis of more than 50 alkenes with good chemo- and stereoselectivity. A preliminary mechanistic study revealed that E-alkene product was generated via sequential alkyne hydrogenation to give Z-alkene intermediate, followed by a Z to E alkene isomerization process.

Inorganic clusters with a [Fe2MoOS3] core - A functional model for acetylene reduction by nitrogenases

We report the first example of a wholly inorganic mimic of a part of the FeMoco active centre of nitrogenases. We detail the synthesis, characterisation and reactivity of two related, transient hydride-containing inorganic clusters, a dihydride complex and a vinyl monohydride complex, which bear the [Fe2MoOS3] portion of FeMoco. The dihydride complex is capable of reducing acetylene to ethylene via the vinyl monohydride complex. In the reaction cycle, a transient low-valent complex was generated by the reductive elimination of H2 or ethylene from dihydride or vinyl monohydride complexes, respectively.

Nickel phosphide nanocatalysts for the chemoselective hydrogenation of alkynes

Well-defined 25 nm nickel phosphide nanoparticles act as a colloidal catalyst for the chemoselective hydrogenation of terminal and internal alkynes. Cis-alkenes are obtained in mild conditions with good conversion and selectivity. The phosphorus inserted in the Ni-P nanoparticles is critical for the selectivity of the nanocatalyst. Mechanistic investigations using isotope labeling provide insight on the reactants interaction with the nanoparticles surface. They pinpoint the occurrence of CH bond cleavage in terminal alkynes during the reaction.

Ruthenium dihydrogen complex for C-H activation: Catalytic H/D exchange under mild conditions

Catalytic H/D-exchange reactions were studied with [Ru(dtbpmp) (η2-H2)(H)2] (1) as catalyst. Under mild reaction conditions (25-75°C) a wide range of arenes and olefins undergo H/D exchange with [D6]benzene. A p

Reactions of vinyldisilanes with ruthenium carbonyl

Reaction of β-styrylpentamethyldisilane (1a) with Ru3(CO)12 afforded β-styryltrimethylsilane (2a) with elimination of a dimethylsilylene unit, while under similar conditions α-isomer 1b yielded 2a together with 1a. Studies on these r