117657-84-8

Upstream product

• 637-59-2 1-Bromo-3-phenylpropane 
• 64740-46-1 1-lithio-3-phenylpropane 
• 300-57-2 allylbenzene 
• 925-90-6 ethylmagnesium bromide 
• 2046-18-6 4-phenylbutyronitrile 
• 2038-62-2 1-fluoro-3-phenylpropane 
• 122-97-4 3-Phenyl-1-propanol 
• 1133215-81-2 (3-phenylpropyl)zinc chloride 
• 1268685-67-1 2-(trideuterothiomethyl)oxazole 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 
• 4119-41-9 1-iodo-3-phenylpropan 
• 5780-97-2 d5-ethylmagnesium bromide 
• 1462-75-5 3-phenylpropylmagnesium bromide 

Relevant academic research and scientific papers

Cyclomagnesation of olefins with ethylmagnesium bromide in the presence of titanium complexes

Cyclomagnesation of terminal and cyclic olefins and 1,2-dienes with RMgHlg and R2Mg in the presence of dichloro(dicyclopentadienyl)titanium(IV) gives non-Grignard cyclic and acyclic organomagnesium compounds. The reaction direction depends on t

Highly Regioselective Copper-Catalyzed Transfer Hydrodeuteration of Unactivated Terminal Alkenes

Catalytic transfer hydrodeuteration of unactivated alkenes is challenging because of the requirement that chemically similar hydrogen and deuterium undergo selective insertion across a π-bond. We now report a highly regioselective catalytic transfer hydro

Decyanation method of nitrile organic compound

The invention provides a decyanation method of a nitrile organic compound. The nitrile organic compound shown in a general formula (1), a sodium reagent, crown ether and a proton donor are subjected to decyanation reaction in an organic solvent I to generate an organic compound shown in a general formula (2). According to the method, a Na/15-crown-5/H2O system is adopted, so that nitrile organic matters can be converted into a decyanation product, and the generation of amine byproducts is inhibited. The new method does not need to use liquid ammonia as a solvent, and is safer and more convenient to operate. The required sodium dispersoid is low in price; and the 15-crown-5 can be recycled and repeatedly used. The method has the advantages of good chemical selectivity, wide substrate application range, good functional group compatibility and the like.

Room Temperature Iron-Catalyzed Transfer Hydrogenation and Regioselective Deuteration of Carbon-Carbon Double Bonds

An iron catalyst has been developed for the transfer hydrogenation of carbon-carbon multiple bonds. Using a well-defined β-diketiminate iron(II) precatalyst, a sacrificial amine and a borane, even simple, unactivated alkenes such as 1-hexene undergo hydrogenation within 1 h at room temperature. Tuning the reagent stoichiometry allows for semi- and complete hydrogenation of terminal alkynes. It is also possible to hydrogenate aminoalkenes and aminoalkynes without poisoning the catalyst through competitive amine ligation. Furthermore, by exploiting the separate protic and hydridic nature of the reagents, it is possible to regioselectively prepare monoisotopically labeled products. DFT calculations define a mechanism for the transfer hydrogenation of propene with nBuNH2 and HBpin that involves the initial formation of an iron(II)-hydride active species, 1,2-insertion of propene, and rate-limiting protonolysis of the resultant alkyl by the amine N-H bond. This mechanism is fully consistent with the selective deuteration studies, although the calculations also highlight alkene hydroboration and amine-borane dehydrocoupling as competitive processes. This was resolved by reassessing the nature of the active transfer hydrogenation agent: experimentally, a gel is observed in catalysis, and calculations suggest this can be formulated as an oligomeric species comprising H-bonded amine-borane adducts. Gel formation serves to reduce the effective concentrations of free HBpin and nBuNH2 and so disfavors both hydroboration and dehydrocoupling while allowing alkene migratory insertion (and hence transfer hydrogenation) to dominate.

Tritiodefluorination of alkyl C–F groups

A straightforward methodology of fluorine substitution by tritium/deuterium is reported. The described method is selective towards the F─C (sp3) group and leaves both the aromatic F─C (sp2) and F2─C (sp3) moieti

Homocoupling of iodoarenes and bromoalkanes using photoredox gold catalysis: A light enabled Au(III) reductive elimination

The formation of homocoupled alkane byproducts have been identified in the reduction of bromoalkanes via photoredox gold catalysis with dimeric Au(I) complexes. This prompted further investigation into the mechanism of formation of these byproducts and the diversity of C-X bonds amenable to this transformation. Examples were found when considering bromoalkanes while a wide variety of iodoarenes underwent this process in good to excellent yields. The light enabled homocoupling of iodoarenes made possible by photoredox gold catalysis is reported.

Catalytic cyclometallation of allylbenzenes by EtAlCl2 and Mg as new route to synthesis of dibenzyl butane lignans

The cyclometallation of allylbenzenes (Ar = Ph, 4-MeO-Ph, 3,4-(MeO)2-Ph) with EtAlCl2 (Et2AlCl) and Mg in the presence of Zr and Ti catalysts (Dzhemilev reaction) has been studied. The reaction run with high diastereoselectivity and gives cyclic organoaluminum compounds, which deuterolysis or hydrolysis gave 2R(S), 3R(S)-dibenzyl butanes with yield of 48-69%. The study of catalyst structure effect on the substrate conversion, reaction chemo- and stereoselectivity showed that the best results were obtained in the case of Cp2ZrCl2 among the tested complexes. The enantioselectivity of neomenthylindenyl or neomenthyltetrahydroindenyl zirconium catalysts in the reaction did not exceed 20%ee. The trans-configuration of the substitutes in the metallacycles formed in the reaction has been proved by X-ray analysis of the hydrolysis product - 2R(S), 3R(S)-dimethyl-1,4-bis[(4′- methoxyphenyl)methyl]-butane. The proposed method could be used for the one-pot diastereoselective synthesis of dibenzyl butane lignans from readily available allylbenzenes.

Synthesis of 2,4- and 2,5-disubstituted oxazoles via metal-catalyzed cross-coupling reactions

The rapid synthesis of 2,4- and 2,5-disubstituted oxazoles via metal-catalyzed cross-coupling reactions is reported. The 4- or 5-position of the corresponding 4- or 5-halogenated 2-butylthiooxazoles was successfully functionalized via Suzuki-Miyaura, Sono

Indium-catalyzed radical reductions of organic halides with hydrosilanes

(Equation Presented) The In(OAc)3-catalyzed reaction of bromo- and iodoalkanes with PhSiH3 in THF at 70°C gave dehalogenated alkanes in good to high yields. In the presence of Et3B and air, the reduction proceeded smoothly at 30°C. When 2,6-lutidine and air were used as additives, the In(OAc)3-catalyzed system enabled an efficient reduction of simple and functionalized iodoalkanes in EtOH. Catalytic use of GaCl3 was found to be effective in the reduction of haloalkanes with poly(methylhydrosiloxane) (PMHS). These catalytic reductions probably involve a radical chain mechanism in which indium or gallium hydride species work as the actual reductants.

A new route of the reaction of EtAlCl2 with α-olefins catalyzed by Ti complexes

A new method for the synthesis of dialkyl(ethyl)alanes by the reaction of EtAlCl2 with α-olefins in the presence of Mg and a catalytic amount of Cp2TiCl2 (Ti(OPri)4, Ti(OBun)4) in THF was developed.