29621-69-0

Upstream product

• 2700-22-3 Benzylidenemalononitrile 
• 98-86-2 acetophenone 
• 109-77-3 malononitrile 
• 100-52-7 benzaldehyde 
• 74-88-4 methyl iodide 
• 34557-54-5 methane 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 5447-87-0 2-(1-phenylethylidene)propanedinitrile 

Downstream Products

• 1244024-78-9 C₂₈H₂₅N₃O₅ 
• 5447-87-0 2-(1-phenylethylidene)propanedinitrile 
• 3461-39-0 3-phenyl-butyric acid methyl ester 
• 4593-90-2 3-phenylbutyric acid 

Relevant academic research and scientific papers

A new and effective method for providing optically active monosubstituted malononitriles: Selective reduction of α,β-unsaturated dinitriles catalyzed by copper hydride complexes

A copper hydride complex, which was generated in situ from CuOt-Bu, BINAP, and PhSiH3, was found to be a highly effective catalyst for the reduction of the CC of α,β-unsaturated dinitriles. In addition to CuOt-Bu, some air and moisture stable C

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

Hydrofluoromethylation of alkenes with fluoroiodomethane and beyond

A process for the direct hydrofluoromethylation of alkenes is reported for the first time. This straighforward silyl radical-mediated reaction utilises CH2FI as a non-ozone depleting reagent, traditionally used in electrophilic, nucleophilic and carbene-type chemistry, but not as a CH2F radical source. By circumventing the challenges associated with the high reduction potential of CH2FI being closer to CH3I than CF3I, and harnessing instead the favourable bond dissociation energy of the C-I bond, we demonstrate that feedstock electron-deficient alkenes are converted into products resulting from net hydrofluoromethylation with the intervention of (Me3Si)3SiH under blue LED activation. This deceptively simple yet powerful methodology was extended to a range of (halo)methyl radical precursors including ICH2I, ICH2Br, ICH2Cl, and CHBr2F, as well as CH3I itself; this latter reagent therefore enables direct hydromethylation. This versatile chemistry was applied to18F-,13C-, and D-labelled reagents as well as complex biologically relevant alkenes, providing facile access to more than fifty products for applications in medicinal chemistry and positron emission tomography.

Photocatalytic Giese-Type Reaction with Alkylsilicates Bearing C,O-Bidentate Ligands

Herein, a photocatalytic Giese-type reaction with alkylsilicates bearing C,O-bidentate ligands as stable alkyl radical precursors has been reported. The alkylsilicates were prepared in one step from organometallic reagents. Not only primary, secondary, and tertiary alkyl radicals, but also elusive methyl radicals, could be generated by using the present reaction system. The generated radicals were trapped by electron-deficient olefins bearing various functional groups to give the desired alkyl adducts. The silicon byproduct can be recovered after the photoreaction. The radical generation process was investigated by theoretical calculations, which provided an insight into the facile generation of methyl radicals from methylsilicate bearing C,O-bidentate ligands.

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).

Homogeneous hydrogenation of electron-deficient alkenes by iridium complexes

The catalytic homogeneous hydrogenation of electron-deficient alkenes (nucleophilic hydrogenation) was achieved in the presence of iridium complexes and a base as co-catalyst. Contrary to hydrogenation of electron-rich alkenes, which is inactivated by bases, the hydrogenation of the electron-deficient alkenes turned out to be base activated. Here, we present a more thorough study on the capacities but also limitations of this new reaction mechanism using screenings of the reaction conditions as well as different Ir complexes and substrates. The formation of a catalytically active Ir complex is proposed. The active complex usually attacks a soft electron-deficient atom, if more than one possibility exists (as shown by density functional theory computations). Additionally, first examples of enantiomeric enrichments in the presence of chiral Ir complexes are presented. The high catalyst load needed and the moderate yields show that the active complex is very unstable under conditions of nucleophilic hydrogenation and is quickly deactivated, which has to be addressed in further studies. Copyright

Rh-catalyzed one-pot reductive alkylation of malononitrile under transfer hydrogenation conditions

Efficient synthesis of monosubstituted malononitriles was achieved by one-pot reductive alkylation of malononitrile with carbonyl compounds via [Cp*RhCl2]2-catalyzed transfer hydrogenation reaction.

Polymer-supported hantzsch 1,4-dihydropyridine ester: An efficient biomimetic hydrogen source for the reduction of ketimines and electron-withdrawing group conjugated olefins

A polymer-supported Hantzsch 1,4-dihydropyridine ester was observed to be a useful selective reducing agent for the reduction of ketimines and electron-withdrawing conjugated olefins. The rate of the reduction of electron-withdrawing conjugated olefins is dependent on the nature of the conjugated substituents and could be enhanced by microwave irradiation. The reduction of (Z)-α-cyano-β-bromomethylcinnamates to cyclopropane derivatives using polymer-supported Hantzsch 1,4-dihydropyridine ester was found to proceed stereoselectively and in good yields.

Nucleophilic homogeneous hydrogenation by iridium complexes

Catalytic homogeneous hydrogenation of 7-methoxy-3-phenylchromone and other substrates was achieved in the presence of cationic iridium complexes and base as co-catalyst. Contrary to common alkene hydrogenation, which is inactivated by base, the hydrogena

Monosubstituted malononitriles: Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes

A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency of the process, and increased the scope of the aromatic aldehydes. Inco