4323-24-4

Upstream product

• 66-77-3 1-naphthaldehyde 
• 108-91-8 cyclohexylamine 
• 4780-79-4 1-naphthalene methanol 
• 201230-82-2 carbon monoxide 
• 90-14-2 1-Iodonaphthalene 

Downstream Products

• 117053-10-8 1-hydroxymethyl-1-methyl-2-benzyl-1,2-dihydronaphthalene 
• 17685-52-8 triiron dodecarbonyl 
• 14489-84-0 N-(naphthalen-1-ylmethyl)cyclohexanamine 
• 99797-48-5 trans-2-phenyl-1,2-dihydro-1-naphthalenylmethanol 
• 98977-81-2 (E)-N-cyclohexyl-N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine 
• 642-29-5 1-benzoylnaphthalene 
• 99797-48-5 (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-phenyl-1,2-dihydronaphthalene 
• 99797-53-2 (1S,2R)-(2-phenyl-1,2-dihydronaphthyl)methan-1-ol 
• 132554-84-8 (1R,2S)-2-phenyl-1,2-dihydronaphthalene-1-carbaldehyde 
• 117076-38-7 (1R,2R)-2-Benzyl-1-methyl-1,2-dihydro-naphthalene-1-carbaldehyde 

Relevant academic research and scientific papers

Vanadium-and chromium-catalyzed dehydrogenative synthesis of imines from alcohols and amines

Vanadium(IV) tetraphenylporphyrin dichloride and chromium(III) tetraphenylporphyrin chloride have been developed as catalysts for the acceptorless dehydrogenation of alcohols. The catalysts have been applied to the direct synthesis of imines in overall good yields from a variety of alcohols and amines. The transformations are proposed to proceed by metal?ligand bifunctional pathways with an outer-sphere transfer of two hydrogen atoms from the alcohol to the metal porphyrin complexes. The results show that vanadium and chromium catalysts can also be employed for the dehydrogenation of alcohols with the release of hydrogen gas, and they may represent valuable alternatives to other catalysts based on Earth-abundant metals.

Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines

Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the by-product(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.

Development and mechanistic investigation of the manganese(iii) salen-catalyzed dehydrogenation of alcohols

The first example of a manganese(iii) catalyst for the acceptorless dehydrogenation of alcohols is presented. N,N′-Bis(salicylidene)-1,2-cyclohexanediaminomanganese(iii) chloride (2) has been shown to catalyze the direct synthesis of imines from a variety of alcohols and amines with the liberation of hydrogen gas. The mechanism has been investigated experimentally with labelled substrates and theoretically with DFT calculations. The results indicate a metal-ligand bifunctional pathway in which both imine groups in the salen ligand are first reduced to form a manganese(iii) amido complex as the catalytically active species. Dehydrogenation of the alcohol then takes place by a stepwise outer-sphere hydrogen transfer generating a manganese(iii) salan hydride from which hydrogen gas is released.

In Situ Generated Cobalt Catalyst for the Dehydrogenative Coupling of Alcohols and Amines into Imines

An in situ formed cobalt catalyst is developed from cobalt(II)bromide, bis[2-(diisopropylphosphino)-4-methylphenyl]amine and zinc metal. The catalyst mediates the acceptorless dehydrogenative coupling of alcohols and amines into imines with the release of hydrogen gas and the transformation is applied to the synthesis of a variety of imines from different alcohols and amines. The mechanism is investigated with labelled substrates and based on the results a cobalt(I) PNP complex is believed to be the catalytically active species which abstracts hydrogen gas from the alcohol through a metal ligand bifunctional pathway.

Molybdenum-Catalyzed Dehydrogenative Synthesis of Imines from Alcohols and Amines

A molybdenum N-heterocyclic carbene catalyst has been developed for the synthesis of imines from primary alcohols and amines with the liberation of dihydrogen. The catalyst is generated in situ from molybdenum hexacarbonyl, 1,3-dicyclohexylimidazolium chloride and potassium tert-butoxide and is further stabilized by the phosphine ligand dppe. Imines are formed in moderate to good isolated yields and a variety of alcohols and amines can be employed in the reaction including anilines. The transformation constitutes the first example of a homogeneous molybdenum-catalyzed acceptorless dehydrogenative coupling with alcohols and is believed to proceed by formation of a cis-coordinated molybdenum bis-N-heterocyclic carbene complex, which performs an oxidative addition to the alcohol, β-hydride elimination and reductive elimination of dihydrogen.

Harnessing Thin-Film Continuous-Flow Assembly Lines

Inspired by nature's ability to construct complex molecules through sequential synthetic transformations, an assembly line synthesis of α-aminophosphonates has been developed. In this approach, simple starting materials are continuously fed through a thin-film reactor where the intermediates accrue molecular complexity as they progress through the flow system. Flow chemistry allows rapid multistep transformations to occur via reaction compartmentalization, an approach not amenable to using conventional flasks. Thin film processing can also access facile in situ solvent exchange to drive reaction efficiency, and through this method, α-aminophosphonate synthesis requires only 443 s residence time to produce 3.22 g h?1. Assembly-line synthesis allows unprecedented reaction flexibility and processing efficiency.

Synthesis and applications of chiral bis-THF in asymmetric synthesis

The synthesis of enantiopure bis-THF is described, starting from d-mannitol. Bis-THF is used as chiral ligand for organolithium reagents in four different reactions. The enantioselectivity provided by this ligand is moderate, and the asymmetric induction is in line with the expected model. Graphical Abstract.

Electronic and steric control in regioselective addition reactions of organolithium reagents with enaldimines

A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic α,β-unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nirtogen atom behaves as a 1,2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl or a bulky aryl group favors 1,4-addition of organolithium reagents. Electronic and steric tuning of a substituent on the imine nitrogen atom for a reaction mode was rationalized on the basis of molecular orbital calculations.

A novel approach for the one-pot preparation of α-amino amides by pd-catalyzed double carbohydroamination

A new domino reaction sequence, a palladium-catalyzed double carbohydroamination, which involves double carbonylation, amine condensation, and hydrogenation from an aryl iodide(1), a primary amine (2), and synthetic gas has been realized as a novel synthetic means for the one-pot synthesis of α-amino amides (3).

Synthesis and Structure-Activity Relationships of Naftifine-Related Allylamine Antimycotics

Naftifine (1) is the first representative of the new antifungal allylamine derivatives.Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals.A tertiary allylamine function seems to be a prerequisite for activity against fungi.By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations.Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.