20441-12-7

Upstream product

• 5350-75-4 benzyltripropylammonium bromide 
• 14657-86-4 N,N-dipropylbenzamide 
• 107-08-4 1-iodo-propane 
• 100-46-9 benzylamine 
• 102-69-2 tri-n-propylamine 
• 71-23-8 propan-1-ol 
• 10546-70-0 N-(n-propyl)benzamide 
• 105-37-3 Ethyl propionate 
• 60-29-7 diethyl ether 
• 5775-34-8 N,N-Dipropyl-chloramine 
• 6921-34-2 benzylmagnesium chloride 
• 100-52-7 benzaldehyde 
• 142-84-7 di-n-propylamine 
• 621-08-9 Dibenzyl sulfoxide 

Downstream Products

• 737-79-1 1,1,3,-triphenyl-1-propene 
• 723-42-2 4-methyl-N,N-dipropylbenzenesulfonamide 
• 1491270-74-6 1,3-dimethyl-3-phenethylindolin-2-one 
• 25173-09-5 N,N-dipropyl-2-phenylacetamide 
• 2532-72-1 N-benzyl-N-methylpropan-1-amine 
• 1531-36-8 dipropylamine-N-carbonitrile 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

N?N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts

The formation of hydrazinium salts by N?N bond formation has typically involved the use of hazardous and difficult to handle reagents. Here, mild and operationally simple conditions for the synthesis of hydrazinium salts are reported. Electrophilic nitrogen transfer to the nitrogen atom of tertiary amines is achieved using iodosylbenzene as oxidant and ammonium carbamate as the N-source. The resulting process is highly chemoselective and tolerant to other functional groups. A wide scope is reported, including examples with bioactive molecules. Insights on the structure of hydrazinium salts were provided by X-ray analysis. (Figure presented.).

Electrochemical deoxygenation of aromatic amides and sulfoxides

The electrochemical deoxygenation of a broad range of aromatic amides was achieved under mild conditions on lead cathodes. Under the optimized reaction conditions, acetal, thienyl, and ether moieties are tolerated. Furthermore, the reduction protocol can be applied to aromatic and aliphatic sulfoxides to obtain the corresponding sulfides. For both aromatic amides and sulfoxides, the deoxygenation reaction ensues without the use of expensive catalysts or hazardous reducing agents. Owing to the high selectivity of the process, simple extraction is sufficient to isolate the product from the substrate. The straightforward purification protocol, the coformation of water, and the use of electric current instead of reducing agents render our method environmentally friendly and economically beneficial. Copyright

A practical regioselective synthesis of alkylthio- or arylthioindoles without the use of smelly compounds such as thiols

A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C2-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.

Cobalt carbonyl-based catalyst for hydrosilylation of carboxamides

The cobalt carbonyl [Co2(CO)8] complex is employed as a useful catalyst for the reduction of tertiary amides to the corresponding tertiary amines using 1,1,3,3-tetramethyldisiloxane (TMDS) and poly(methylhydrosiloxane) (PMHS) as silane reagents under thermal (100 °C) or photo-assisted conditions (UV, 350 nm at room temperature). Of particular interest, a low catalytic amount (0.5 mol%) of [Co2(CO)8] is used to perform the reaction with 2.2 equiv. of PMHS at 100 °C for 3 h. This reaction is the first example of a cobalt-catalyzed hydrosilylation of amides. Copyright

Phosphane-pyridine iron complexes: Synthesis, characterization and application in reductive amination through the hydrosilylation reaction

A series of 6 cyclopentadienyl phosphanyl-pyridine piano-stool iron complexes was prepared in good yields, characterized, and studied in the catalytic reductive amination of benzaldehyde derivatives through hydrosilylation reactions by using polymethylhydrosiloxane as the hydrosilane source and in dimethylcarbonate as the solvent at 40 °C. Single-crystal X-ray structural analyses were performed for all the complexes. A series of 6 cyclopentadienyl phosphanyl-pyridine piano-stool iron complexes was prepared, characterized, and studied in the catalytic reductive amination of benzaldehyde derivatives in dimethylcarbonate through hydrosilylation reactions by using polymethylhydrosiloxane as the hydrosilane source. Copyright

Reductive amination of carbonyl compounds over silica supported palladium exchanged molybdophosphoric acid catalysts

Palladium exchanged molybdophosphoric acid supported on silica is reported as a highly effective catalyst for direct reductive amination of carbonyl compounds. The catalysts are characterized by X-ray diffraction and FT-infrared spectroscopy. The characterization results support the existence of Keggin ion of heteropoly molybdate on silica. The catalyst is facile, water tolerable and environmentally benign for reductive amination. A variety of secondary and tertiary amines can be synthesized over this catalyst in excellent yields under mild reaction conditions. A plausible reaction mechanism is proposed for the reductive amination of carbonyl compounds over this catalyst.

Borrowing hydrogen in water and ionic liquids: Iridium-catalyzed alkylation of amines with alcohols

The use of [Cp*IrI2]2 as an efficient catalyst for the alkylation of amines by alcohols in either water or ionic liquid is described. Primary amines are converted into secondary amines, and secondary amines into tertiary amines in the absence of base, and the chemistry has been applied to the synthesis of the analgesic fentanyl. The conversion of primary amines into N-heterocycles by the reaction with diols is also described, along with the N-alkylation of sulfonamides.

Iron-catalyzed, hydrogen-mediated reductive cyclization of 1,6-enynes and diynes: Evidence for bis(imino)pyridine ligand participation

(Chemical Equation Presented) The bis(imino)pyridine iron dinitrogen complex (iPrPDI)Fe(N2)2 catalyzes the hydrogen-mediated reductive cyclization of enynes and diynes with turnover frequencies comparable to those of established precious metal catalysts. Amino, oxygenated, and carbon-based substrates are readily cyclized to the corresponding hetero- and carbocycles with 5 mol % iron and 4 atm H2 at 23°C. Stoichiometric reactions between selected substrates and the iron compound under a N2 atmosphere established transfer dehydrogenation from an isopropyl aryl substituent to either the enyne or diyne substrate. In situ monitoring of the catalytic reaction by 1H NMR spectroscopy coupled with deuterium labeling experiments established rapid cyclization followed by turnoverlimiting hydrogenation. Copyright

Ruthenium-catalyzed /V-alkylation of amines and sulfonamides using borrowing hydrogen methodology

The alkylation of amines by alcohols has been achieved using 0.5 mol percent [Ru(p-cymene)CI2]2 with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. A/-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols requiremore forcing conditions than primary alcohols but are still effective a lkylating agents in the presence of this catalyst.

Reductive amination with 5-ethyl-2-methylpyridine borane

We report a new amine borane, 5-ethyl-2-methylpyridine borane complex (PEMB) useful for reductive aminations of ketones and aldehydes in methanol or neat. Two of the three hydrides on PEMB are effectively utilized maximizing the economy of the reagent.