16659-09-9

Upstream product

• 109-72-8 n-butyllithium 
• 100-47-0 benzonitrile 
• 100-46-9 benzylamine 
• 693-03-8 n-butyl magnesium bromide 
• 98-80-6 phenylboronic acid 
• 62-53-3 aniline 
• 1009-14-9 phenyl butyl ketone 
• 109-65-9 1-bromo-butane 
• 10229-55-7 (E)-benzaldehyde O-ethyl oxime 

Downstream Products

• 51110-18-0 ((Z)-1-Isothiocyanato-pent-1-enyl)-benzene 
• 133682-44-7 1-isopropoxy-4-propyl-3-phenyl-2-aza-1,3-butadiene 
• 133682-43-6 1-isopropoxy-4-propyl-3-phenyl-2-aza-1,3-butadiene 
• 1388044-68-5 (Z)-N-(1-phenylpentylidene)pent-1-yn-1-amine 
• 1592078-16-4 (Z)-2-(4-methoxyphenyl)-N-(1-phenylpentylidene)ethynamine 
• 1592078-25-5 (Z)-2-(4-methoxyphenyl)-3-phenylhept-3-enenitrile 
• 1592078-26-6 2-(4-methoxyphenyl)-3-phenylhept-2-enenitrile 
• 197163-72-7 4-n-butyl-2-phenylquinazoline 
• 1009-14-9 phenyl butyl ketone 
• 875856-17-0 1-(o-tolyl)pentan-1-imine 
• 10264-18-3 N-phenylpentanamide 

Relevant academic research and scientific papers

Introducing Glycerol as a Sustainable Solvent to Organolithium Chemistry: Ultrafast Chemoselective Addition of Aryllithium Reagents to Nitriles under Air and at Ambient Temperature

Edging closer towards developing air and moisture compatible polar organometallic chemistry, the chemoselective and ultrafast addition of a range of aryllithium reagents to nitriles has been accomplished by using glycerol as a solvent, at ambient temperature in the presence of air, establishing a novel sustainable access to aromatic ketones. Addition reactions occur heterogeneously (“on glycerol conditions”), where the lack of solubility of the nitriles in glycerol and the ability of the latter to form strong intermolecular hydrogen bonds seem key to favouring nucleophilic addition over competitive hydrolysis. Remarkably, PhLi exhibits a greater resistance to hydrolysis working “on glycerol” conditions than “on water”. Introducing glycerol as a new solvent in organolithium chemistry unlocks a myriad of opportunities for developing more sustainable, air and moisture tolerant main-group-metal-mediated organic synthesis.

A convenient synthesis of tertiary carbinamines via N-aluminum ketimines

Reaction of N-unsubstituted ketimines with organoaluminum reagents prepared from allylic and propargylic halides, allows to prepare, in good yields, tertiary carbinamines with three different groups (phenyl, alkyl and α-unsaturated group) on die tertiary carbon center.

Combination of air/moisture/ambient temperature compatible organolithium chemistry with sustainable solvents: Selective and efficient synthesis of guanidines and amidines

Highly-efficient and selective fast addition of in situ generated lithium amides [LiN(H)R] (obtained via an acid-base reaction between n-BuLi and the desired primary amine) into carbodiimides (R-NCN-R) or nitriles (R-CN) has been studied, for the first ti

Copper-catalyzed [2+3]-annulation of N-H imines with vinyl azides: Access to polyaryl 2: H -imidazoles

A practical method for the synthesis of 2H-imidazoles via a [2+3] annulation of N-H imines with vinyl azides using a copper catalyst is developed. In this conversion, environmentally friendly oxygen is used as the sole oxidant and N2 and H2O are the only by-products. The catalytic transformation, operating under mild conditions, is operationally simple and is considered as a readily available catalytic system having good substrate and functional compatibility with high atom-efficiency without the need for additional ligands or additives.

Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines

N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation of N-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described.

Selective Oxidative [4+2] Imine/Alkene Annulation with H2 Liberation Induced by Photo-Oxidation

The oxidative [4+2] annulation reaction represents an elegant and versatile synthetic protocol for the construction of six-membered heterocyclic compounds. Herein, a photoinduced oxidative [4+2] annulation of NH imines and alkenes was developed by utilizing a dual photoredox/cobaloxime catalytic system. Various multisubstituted 3,4-dihydroisoquinolines can be obtained in good yields. This method is not only obviated the need of stiochiometric amounts of oxidants but also exhibited excellent atom economy by generating H2 as the only byproduct. Remarkably, high regioselectivity and trans diastereoselectivity can be achieved in this transformation even if the Z/E mixture of alkenes were employed.

Nickel-Catalyzed 1,2-Aminoarylation of Oxime Ester-Tethered Alkenes with Boronic Acids

A nickel-catalyzed 1,2-aminoarylation of oxime-ester-tethered alkenes with boronic acids was developed. A variety of pyrroline derivatives were synthesized in good yields via the successive formation of C(sp3)-N and C(sp3)-C(sp2) bonds. For cyclobutanone-derived oxime esters, the reaction provided aliphatic nitriles incorporating an aromatic group in the γ-position. A mechanism involving iminyl radical and carbon-centered radical intermediates was proposed.

Organocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles

An unprecedented organocatalytic enantioselective vinylogous Michael addition/Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones 3 employing novel 1,3-indandione-derived pronucleophiles 1a-g and nitroalkenes 2. Following a very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43-98% yield, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione (1h) was used as a pronucleophile, no cyclization was observed, and only Michael addition adducts 4a-x were furnished in very good yields and excellent enantioselectivities. (Chemical Equation Presented).

Nickel catalyzed cross-coupling and amination reactions of aryl nitriles

Aryl nitriles have been found to participate in cross-coupling and amination reactions via nickel-catalyzed activation of the C-CN bond. With the development of these synthetically useful transformations, aryl nitriles can now be considered along with ary

Process for the preparation of tertiary carbinamines

This invention relates to a novel process for the preparation of tertiary carbinamines by double addition of organolanthanide reagents, especially organocerium reagents, to nitriles. It further relates to the preparation of such amines by the addition of