88738-45-8

Upstream product

• 68761-08-0 (1-phenyl-butylidene)-malononitrile 
• 100-52-7 benzaldehyde 
• 74-98-6 propane 
• 2700-22-3 Benzylidenemalononitrile 

Relevant academic research and scientific papers

Iron-Catalyzed Photoredox Functionalization of Methane and Heavier Gaseous Alkanes: Scope, Kinetics, and Computational Studies

Herein, we report the development of the photocatalytic C-H functionalization of methane, ethane, and heavier gaseous alkanes with good yields and selectivity, broad scope (57 examples), mild conditions, and low cost. Kinetics and density functional theor

Convenient C(sp3)-H bond functionalisation of light alkanes and other compounds by iron photocatalysis

Light alkanes are natural organic carbon sources and widely distributed in nature. Transforming them into value-added fine chemicals affords attractively economic and ecological benefits as well as enormous chemical challenges. Herein, we report a practical iron-catalysed photoredox system for C(sp3)-H transformation of ethane, propane, and other light alkanes to C-N and C-C bonds under ambient temperature. The present method with abundant and inexpensive iron salts as photocatalysts exhibits high catalytic efficiency (turnover number up to 8000), mild conditions, and the convenience of being purified and scaled up without chromatography. A photo-induced ligand-to-metal charge transfer between Fe(iii) and Cl- generates a highly active chlorine radical that sequentially acts as hydrogen atom transfer catalyst. Therefore, the sustainable, convenient, and environmentally friendly system will find wide applications in high-value-added transformation of natural alkanes with novel inspiration not only for organic synthesis, but also for designing catalytically active organic/inorganic materials. This journal is

C(sp3)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow

Direct activation of gaseous hydrocarbons remains a major challenge for the chemistry community. Because of the intrinsic inertness of these compounds, harsh reaction conditions are typically required to enable C(sp3)-H bond cleavage, barring potential applications in synthetic organic chemistry. Here, we report a general and mild strategy to activate C(sp3)-H bonds in methane, ethane, propane, and isobutane through hydrogen atom transfer using inexpensive decatungstate as photocatalyst at room temperature. The corresponding carbon-centered radicals can be effectively trapped by a variety of Michael acceptors, leading to the corresponding hydroalkylated adducts in good isolated yields and high selectivity (38 examples).

Lewis Acid-prompted Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds by 2-Phenylbenzothiazoline (2-Phenyl-2,3-dihydrobenzothiazole)

Reduction of various α,β-unsaturated ketones (3a-g) and (4a-d) in methanol by the benzothiazoline (1) in the presence of aluminium chloride gives, in all cases, the corresponding saturated ketones (5a-g) and (6a-d)without any of the unsaturated or saturated alcohol.Reduction of α,β-unsaturated esters (7a,b) similarly gives the saturated esters (9a,b), while reaction of cinnamaldehyde (8) with compound (1) does not occur at all.Among the Lewis acids examined, aluminium chloride gives the best results.Reduction of 2'-azachalcone (21) with 2-phenylbenzothiazoline reveals that, in the reduction product, the deuterium atom is located at the β-position with respect to the carbonyl group.The result obtained from the reduction of the same substrate with compound (1) in methanol shows that no incorporation of a hydrogen atom from the solvent takes place and suggests (indirectly) that the introduced hydrogen atom at the α-position of the product comes from the benzothiazoline (1).The reaction of (Z)-1,2-dibenzoyl-1,2-diphenylethylene (30) with compound (1) in the presence of aluminium chloride stereospecifically yields meso-1,2-dibenzoyl-1,2-diphenylethane (31).This shows that the transfer of two hydrogens from compound (1) to the carbon-carbon double bond of the enone proceeds via cis-addition.Experiments with ethyl phenylpropiolate (28) also support cis-reduction for the present conjugate reduction.These results are interpreted in terms of a mechanism involving synchronous transport of a pair of hydrogens from the benzothiazoline (1); i.e a cyclic addition of the two hydrogens either in exact or nearly exact concurrence.

In Situ Generation and Synthetic Application of 2-Phenylbenzimidazoline to the Selective Reduction of Carbon-Carbon Double Bonds of Electron-Deficient Olefins

2-Phenylbenzimidazoline (PBI) as a mild, selective, and convenient reducing agent was efficiently generated in situ from o-phenylenediamine and benzaldehyde in alcohols.A generally applicable method for the selective reduction of carbon-carbon double bonds of a variety of electron-deficient olefins with an alcoholic solution of PBI is described.The reduction of α,β-unsaturated ketones to the corresponding saturated ketones could also be accomplished (but, less effectively) with PBI with the aid of a Lewis-acid catalyst. 1-Methyl-2-(o-nitrophenyl)benzimidazoline prepared and isolated by the reaction of o-nitrobenzaldehyde with N-methyl-o-phenylenediamine reduced benzylidenemalononitrile to give benzylmalononitrile and 1-methyl-2-(o-nitrophenyl)benzimidazoline in high yields.This shows the validity of PBI to be the actual reducing species in the present reduction system.From a mechanistic study, the present reductions could be interpreted in terms of a mechanism involving a synchronous transport of a pair of hydrogens or a sequential transfer of a hydride and a proton from PBI to the olefins.