254992-96-6

Upstream product

• 1613-92-9 (E)-N-benzylidene-4-toluidine 
• 1730-25-2 allylmagnesium bromide 
• 24850-33-7 allyltributylstanane 
• 100-52-7 benzaldehyde 
• 106-49-0 p-toluidine 
• 99-99-0 1-methyl-4-nitrobenzene 
• 2272-45-9 benzal-p-toluidine 
• 106-95-6 allyl bromide 
• 5405-15-2 N-benzyl-N-(4-methylphenyl)amine 
• 2551-83-9 allyltrimethoxysilane 
• 33499-39-7 4-methylbenzaldehyde-O-methyl oxime 
• 591-51-5 phenyllithium 
• 107-18-6 allyl alcohol 

Downstream Products

• 853-36-1 1-(4-methylphenyl)-2,5-diphenylpyrrole 
• 280573-71-9 4,6-dimethyl-2-phenyl-1,2,3,4-tetrahydro-quinoline 
• 609354-27-0 4-phenyl-4-p-tolylamino-butan-2-ol 

Relevant academic research and scientific papers

Regio- and diastereoselective three-component syntheses of homoallylic amines in aqueous media catalyzed by Bronsted acids

A systematic investigation into the three component allylation reaction of aldehydes, amines, and allyltributylstannanes catalyzed by Brensted acids in aqueous media was reported. The reaction was effective and able to produce homoallylic amines in modera

Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ

A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.

Organic Photoredox-Catalyzed Synthesis of δ-Fluoromethylated Alcohols and Amines via 1,5-Hydrogen-Transfer Radical Relay

The hydrotrifluoromethylation of benzyl-protected homoallylic alcohol and amine derivatives catalyzed by 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) was developed. This reaction delivered δ-fluoromethylated free alcohols and amines with in situ deprotection of benzyl protecting group under mild irradiation conditions. 4CzIPN was found to be a competent metal-free photoredox catalyst for activating several types of fluoromethylation reagents including CF3SO2Cl, Togni's reagent, and 2-bromo-2,2-difluoroacetate via oxidative quenching and also CF3SO2Na through reductive quenching to allow direct hydrotrifluoromethylation of simple alkenes and Michael acceptors.

A silver triflate-catalyzed cascade of in situ-oxidation and allylation of arylbenzylamines

A silver-triflate catalyzed cascade of in situ-oxidation and allylation of arylbenzylamines is reported. The 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate is employed as a mild oxidant which is compatible with both catalyst and ligand. Racemic BINAP is also utilized to assist with the catalyst in regulating the yields of products. Various homoallylic amines are obtained in 39–99% yields.

Synthesis of homoallylic amines and acylhydrazides by tin powder-promoted multicomponent one-pot allylation reactions

An efficient process for the synthesis of homoallylic amines and N′-homoallylic hydrazides is developed from the one-pot reaction of carbonyl compounds, amines or N-acylhydrazines, allyllic bromide and tin powder using water as solvent. N-Acylhydrazines are found to be more reactive than amines in these processes. They can react not only with aldehydes but also with ketones to give the corresponding N′-homoallylic hydrazides. Copyright

Synthesis of polysubstituted pyrroles via Pd-catalyzed oxidative alkene C-H bond arylation and amination

A novel Pd(II)-catalyzed oxidative approach to construct polysubstituted pyrroles from N-homoallylicamines and arylboronic acids was developed. This transformation is supposed to proceed through cascade formation of C-C and C-N bonds via oxidative arylation of unactive alkenes, followed by intramolecular aza-Wacker cyclization.

Sn-mediated one-pot four-component allylation of aldimines

A convenient and facile method for the synthesis of homoallylic amines was disclosed. The one-pot reaction of aldehydes, aromatic amines and allylic bromide with tin powder at room temperature could afford the homoallylic amines in good to excellent yield

MgI2 etherate-catalyzed three-component allylation: A facile and efficient synthesis of homoallylic amines

MgI2 etherate-catalyzed three-component condensation of aldehydes, amines and allyltributylstannane under mild and neutral reaction conditions was developed and efficiently afforded the corresponding homoallylic amine derivatives in good to exc

Synthesis, structure and catalytic properties of CNN pincer palladium(II) and ruthenium(II) complexes with N-substituted-2-aminomethyl-6-phenylpyridines

N-substituted-2-aminomethyl-6-phenylpyridines 2a-c have been easily prepared from commercially available 6-bromo-2-picolinaldehyde in two steps. Reaction of 2a-c with PdCl2 in toluene in the presence of triethylamine gave the CNN pincer Pd(ii) complexes 3a-c in 18-28% yields. The CNN pincer Ru(ii) complex 5 containing a Ru-NHR functionality could be obtained in a 71% yield by treatment of 2c with a Ru(ii) precursor instead of PdCl 2. Additionally, the related CNN pincer Ru(ii) complex 7 containing a Ru-NH2 functionality has been synthesized by the reaction of 2-aminomethyl-6-phenylpyridine with the same Ru(ii) precursor in a 68% yield. All the new compounds were characterized by elemental analysis (MS for ligands), 1H, 13C NMR, 31P{1H} NMR (for Ru complexes) and IR spectra. Molecular structures of Pd complex 3c as well as Ru complexes 5 and 7 have been determined by X-ray single-crystal diffraction. The obtained Pd complexes 3a-c were effective catalysts for the allylation of aldehydes as well as for three-component allylation of aldehydes, arylamines and allyltributyltin and their activity was found to be much higher than a related NCN Pd(ii) pincer in the allylation of aldehyde. On the other hand, the two new CNN pincer Ru(ii) complexes 5 and 7 displayed excellent catalytic activity in the transfer hydrogenation of ketones in refluxing 2-propanol with the latter being much more active. The final TOF values were up to 4510 h-1 with 0.01 mol% of 5 and 220800 h-1 with 0.005 mol% of 7, respectively. The Royal Society of Chemistry 2011.

Titanocene(III) chloride mediated radical induced allylation of aldimines: Formal synthesis of C-linked 4′-deoxy aza-disaccharide

Titanocene(III) chloride (Cp2TiCl) mediated radical induced allylation of aldimines for the preparation of homoallyl amines is described. The radical was generated from the allyl bromide using Cp2TiCl as the radical source. Formal synthesis of C(4)-C(5′)-linked 4′-deoxy aza-disaccharide is demonstrated and a study toward the bicyclic skeleton of alkaloids was also accomplished. The radical initiator Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp 2TiCl2) and Zn dust in THF under argon.