15258-46-5

Upstream product

• 7575-57-7 allyl benzenesulfonate 
• 106-49-0 p-toluidine 
• 107-18-6 allyl alcohol 
• 107-05-1 3-chloroprop-1-ene 
• 2101-86-2 p-methylazidobenzene 
• 106-95-6 allyl bromide 
• 556-56-9 allyl iodid 
• 1172142-53-8 N-allyl-N-(4-methylphenyl)-2-nitrobenzenesulfonamide 
• 3481-07-0 N-allyl-N-methyl-4-methylaniline 
• 22774-64-7 N-propargyl-4-methylaniline 
• 14618-59-8 N-(tert-butoxycarbonyl)-4-methylaniline 
• 6728-21-8 allyl mesylate 
• 1826-67-1 vinyl magnesium bromide 
• 156704-05-1 (3-Methyl-indazol-1-ylmethyl)-p-tolyl-amine 

Downstream Products

• 861616-23-1 N-allyl-N'-phenyl-N-p-tolyl-thiourea 
• 913169-20-7 N-allyl-N-benzyl-4-methylaniline 
• 59816-83-0 2-allyl-4-methyl-phenylamine 
• 90874-56-9 (±)-2,5-dimethylindoline 
• 66236-05-3 N-allyl-4-methyl-N-(4-methylphenyl)benzenesulfonamide 
• 1172142-65-2 methyl 2-[N-allyl-N-(4-methylphenyl)sulfamoyl]acetate 
• 1202021-50-8 C₁₇H₂₂BrN 
• 1202021-55-3 C₂₁H₂₂BrN 
• 1418217-96-5 2-allyl-4-methyl-N-(prop-2-ynyl)aniline 
• 1418218-04-8 N-(2-allyl-4-methylphenyl)-N-(prop-2-ynyl)acrylamide 
• 1431610-52-4 N-(2-fluoropropyl)-4-methylaniline 
• 340011-47-4 N-allyl N-(4-methylphenyl)acrylamide 
• 167558-64-7 1-(4-methyl-phenyl)-3-methyl-1H-indole 
• 66236-12-2 N-(2-allyl-4-methylphenyl)methanesulfonamide 

Relevant academic research and scientific papers

Pentacoordinated Carboxylate π-Allyl Nickel Complexes as Key Intermediates for the Ni-Catalyzed Direct Amination of Allylic Alcohols

Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)2] and 1,1′-bis(diphenylphosphino)ferrocene was effectively enhanced by adding nBu4NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu4NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated η3-allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.

Fused ring compound and preparation method thereof

The invention provides a fused ring compound and a preparation method thereof. In the method, precursor compounds A and B prepared under the conditions of triethylamine as a base, DMF as a solvent andpalladium acetate and triphenylphosphine as a catalyst react to generate a series of new fused ring compounds with a unique stereoselectivity. Compared with the conventional fused ring compound, thefused ring compound prepared by the invention has a more complicated structure, a mild reaction condition and a high reaction yield. The fused ring compound also shows a broader prospect of use in chemical production and clinical medicine.

Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor

We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.

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.

Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon

Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy-to-execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl-anilines and allyl-phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.

Indole compound and synthesizing and application methods thereof

The invention relates to an indole compound and synthesizing and application methods thereof. The indole compound is prepared by selecting specific substituent groups. Experiments find that the indolecompound can achieve good inhibiting effects on prostatic cancer, good in drug-resistance-proofness and low in side effects when applied as an anti-cancer drug; besides, the synthesizing method of the indole compound comprises subjecting a compound with the structure shown as the formula (II), palladium acetate, benzoquinones and organic acids to reaction in solvent to obtain the indole compoundwith the structure shown as the formula (I). Experiment results show that the synthesizing method of the indole compound is low in requirements on substrate and high in product yield.

One-pot Construction of Difluorinated Pyrrolizidine and Indolizidine Scaffolds via Copper-Catalyzed Radical Cascade Annulation

A convenient approach to the synthesis of diverse difluorinated nitrogen-containing polycycles via a copper-catalyzed radical cascade annulation of amine-containing olefins and ethyl bromodifluoroacetate was developed. Three new bonds, including a Csp3 ?CF2 and two C?N bonds, are forged simultaneously in this strategy. Through this strategy, a series of difluorinated pyrrolizidine and indolizidine derivatives have been conveniently synthesized in good yields. (Figure presented.).

A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols

The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).

Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes

Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).

Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate

A mild aerobic intramolecular aminoacetoxylation method for the synthesis of pyrrolidine and indoline derivatives was achieved using molecular oxygen as the oxidant. A catalytic NOx species acts as an electron transfer mediator to access a high-valent palladium intermediate as the presumed active oxidant.