6907-75-1

Upstream product

• 109-73-9 N-butylamine 
• 98-86-2 acetophenone 
• 6077-10-7 bis(phenylethynyl)mercury 
• 536-74-3 phenylacetylene 
• 762-04-9 phosphonic acid diethyl ester 
• 98-85-1 1-Phenylethanol 

Downstream Products

• 118825-56-2 Propyl-[2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-(1-phenyl-ethyl)-heptyl]-amine 
• 150056-96-5 1-butyl-4-hydroxy-3,6-diphenyl-2-pyridone 
• 92444-77-4 N-butylacetamidostyrene 
• 150057-11-7 1-butyl-4-hydroxy-3-methoxycarbonyl-6-phenyl-2-pyridone 
• 5412-64-6 butyl-(1-phenyl-ethyl)-amine 
• 7126-64-9 1-butyl-2-phenyl-1H-indole 
• 19302-34-2 (S)-(-)-N-(1-phenylethyl)butylamine 
• 628729-62-4 (R)-(+)-N-butyl-N-(α-phenylethyl)amine 
• 1186336-25-3 C₁₄H₂₁NO 
• 1415315-21-7 C₁₂H₁₄F₂ 
• 1415314-94-1 C₁₀H₁₀F₂O 
• 395-01-7 2,2-difluoro-1-phenylethanone 

Relevant academic research and scientific papers

Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines

Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands.

Diethylsilane as a Powerful Reagent in Au Nanoparticle-Catalyzed Reductive Transformations

Diethylsilane (Et2SiH2), a simple and readily available dihydrosilane, that exhibits superior reactivity, as compared to monohydrosilanes, in a series of reductive transformations catalyzed by recyclable and reusable Au nanoparticles (1 mol-%) supported on TiO2. It reduces aldehydes or ketones almost instantaneously at ambient conditions. It can be used in a one pot rapid reductive amination procedure, in which premixing of aldehyde and amine is required prior to the addition of the reducing agent and the catalyst, even in a protic solvent. An unprecedented method for the synthesis of N-arylisoindolines is also shown in the reductive amination between o-phthalaldehyde and anilines. In this transformation, it is proposed that the intermediate N,2-diphenylisoindolin-1-imines are reduced stepwise to the isoindolines. Finally, Et2SiH2 readily reduces amides into amines in excellent yields and shorter reaction times relative to previously known analogous nano Au(0)-catalyzed protocols.

Au nanoparticle-immobilized L-cysteine-paired porous ionic copolymer as an efficient catalyst for additive-free oxidative coupling of alcohols and amines

Herein, an L-cysteine-paired ionic copolymer (DVB-[MimLcy]n) with mesoporosity was prepared by free radical copolymerization of divinylbenzene (DVB) and imidazolium ionic liquids (ILs), followed by anion-exchange with L-cysteine. Because of the rich functional groups of –NH2, –SH, and –COO– and the porous framework, the DVB-[MimLcy]3 was revealed to be an ideal stabilizer for metal nanoparticles (NPs). Highly uniform dispersed small Au NPs (2–3 nm) immobilized on DVB-[MimLcy]3 (Aua/DVB-[MimLcy]3) can act as an efficient heterogeneous catalyst for additive-free synthesis of imines through coupling of a broad range of alcohols and organic amines and can be easily recovered and steadily reused several times.

Formation of chiral fluoroalkyl products through copper-free enantioselective allylic alkylation catalyzed by an NHC ligand

A valuable Cu-free protocol is reported where an NHC ligand has been employed to form quaternary carbon centers bearing fluoroalkyl units. The results obtained, from this allylic substitution, are better in terms of enantioselectivity and regioselectivity compared to the copper catalyzed system.

Modular synthesis of indoles from imines and o-dihaloarenes or o-chlorosulfonates by a Pd-catalyzed cascade process

A detailed study of the scope of a new Pd-catalyzed synthesis of indolesfrom 1,2-dihaloarenes and o-halobenzene sulfonates and imines is descri bed. The cascade reaction comprises an imine a-arylation ollowed by an intramolecular C-N bond-forming reaction promoted by the same Pd catalyst. The reaction with 1,2-dibromobenzene shows wide scope and allows the introduction of aryl, alkyl, and vinyl substituents at different positions of the five-membered ring of the indole. The regioselective synthesis of indoles substituted in the six-membered ring can be carried out by employing o-dihalobenzene derivatives with two different halogens, taking advantage of the different reactivities of I, Br, and Cl in oxidative addition reactions. This paper also introduces a method for the efficient cleavage of the N-t-butyl group, thus allowing for the preparation of N-H indoles through the same methodology. Finally, the reaction with o-halosulfonates has been studied. The best substrates are o-chlorononaflates, which lead to indoles in very high yield. The reaction is particularlyappropriate for the synthesis of the challenging 6-substituted indoles. In view of the availability of o-chlorophenols, which are direct precur sors of the chlorononaflates, this reaction represents an efficient entry into indoles substituted in the six-membered ring. The concept is illustrated by the preparation of a 4,6-disubstituted indole from naturally occurring anethole.

1,1′-Binaphthyldiamine-based lewis bases as readily available and efficient grganocatalysts for the reduction of N-Aryl and N-Alkyl ketimines

The development of simple, low-cost, efficient, and sustainable routes to enantiomerically pure amines is a topic of extraordinary interest, specially in view of future industrial applications. In this context, we wish to report a chemical and stereochemical efficient synthesis of chiral amines through the Lewis base activated trichlorosilane reduction of ketimines. An organocatalyst, easily prepared in a single step through the condensation of picolinic acid and commercially available 1,1′-binaphthyldiamine, is the key element of this metal-free methodology, that allowed the synthesis of chiral secondary and primary amines in high yields and stereose-lectivity. Noteworthy, such catalysts are able to promote the reduction of N-alkyl ketimines, often in quantitative yield and up to 87% enantioselectivity; it: is worth mentioning that for such transformations only one other organocatalytic system has been reported so far.

Chiral Lewis base promoted trichlorosilane reduction of ketimines. An enantioselective organocatalytic synthesis of chiral amines

The reduction of the carbon-nitrogen double bond is an important transformation. Here we report our studies on a family of chiral organic catalysts able to promote the stereoselective reduction of ketimines with trichlorosilane. The very cheap, metal-free catalysts were easily prepared in one step from commercially available products, namely a chiral aminoalcohol and picolinic acid derivatives. The catalyst structure was extensively modified in a study that allowed to identify an extremely active species, able to promote the reduction on a large variety of substrates with high efficiency (up to 95% ee). A three component methodology has been also developed, where the enantiomerically enriched amine was isolated after performing the reaction by mixing a ketone and an amine in the presence of trichlorosilane and the catalyst. Its synthetic potentiality was demonstrated by employing the present metal-free catalytic procedure in the preparation of (S)-metolachlor, a potent and widely used herbicide.

Direct electrophilic α-fluorination of imines: Efficient synthesis of mono-and difluoroimines

(Chemical Equation Presented) A mild and efficient procedure to synthesize α-fluoro- and α,α-difluoroimines was developed. Various N-alkylimines derived from acetophenones were successfully monofluorinated using NFSI (N-fluorobenzenesulfonimide) in a mixture of CH3CN and DMF at 0°C. Alternatively, the same procedure without DMF gave rise to difluorinated imines when performed at room temperature. The obtained α- and α,α-difluorinated imines were subsequently reduced to give the corresponding β-fluoro- and β,β-difluoroamines in good yield.

Nucleophilic addition to carbonyl compounds, competition between hard (amine) and soft (phosphite) nucleophile

In the Kabachnik Fields reaction mixture, two nucleophiles: dialkyl phosphite and the amine compete for the electrophilic carbonyl compound. Reaction mixture composition studies, kinetic studies as well as theoretical calculations, indicate that the softe

ON THE REVERSIBILITY OF HYDROXYPHOSPHONATE FORMATION IN THE KABACHNIK-FIELDS REACTION

The reversibility of hydroxyphosphonate synthesis in the Kabachnik-Fields synthesis was studied. It was found that in all studied cases which included aliphatic and aromatic aldehydes or ketones the hydroxyphosphonates decompose to the starting ketone and