24431-14-9

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 201230-82-2 carbon monoxide 
• 108-91-8 cyclohexylamine 
• 106-43-4 para-chlorotoluene 
• 104-88-1 4-chlorobenzaldehyde 
• 873-76-7 para-Chlorobenzyl alcohol 
• 46459-32-9 N-(4-chlorobenzyl)-N-cyclohexylamine 

Downstream Products

• 46459-32-9 N-(4-chlorobenzyl)-N-cyclohexylamine 
• 1245501-92-1 1-[(4-chlorophenyl)(cyclohexylamino)methyl]naphthalen-2-ol 
• 134-85-0 4-chlorobenzophenone 
• 99-91-2 para-chloroacetophenone 

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.

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

Synthesis and molecular docking studies of imines as α-glucosidase and α-amylase inhibitors

Imine functionality is found in many compounds with important biological activity. Thus, the development of novel synthetic approaches for imines is important. In this work, it is propose an easy, eco-friendly and straightforward synthesis pathway of aryl imines under microwave irradiation catalyzed by Alumina-sulfuric acid. In addition, the in vitro enzymatic inhibition, antioxidant activity and molecular docking studies were performed. The aryl imines were isolated with yields in the range of 37–94%. All aryl imines synthesized were evaluated for in vitro inhibitory potential against α-glucosidase and α-amylase enzymes and the results exhibited that the most of the compounds displayed inhibitory activity against both enzymes. The (E)-1-(4-nitrophenyl)-N-(pyridin-2-yl)methanimine (3d) was 1.15-fold more active than acarbose against α-amylase whilst the (E)-1-phenyl-N-(pyridin-2-yl)methanimine (3c) displayed similar activity that acarbose against α-glucosidase. The molecular docking studies in α-glucosidase and α-amylase reveal that aryl imines mainly establish an H-bond with the R2-subtituent and hydrophobic interactions with the R1-subtituent. The docking analysis reveals these synthetic aryl imines 3d-i interact in same active site than acarbose drug in both enzymes.

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.

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.

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.

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.

MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS

The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C-C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di- lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.

Sustainable iron-catalyzed direct imine formation by acceptorless dehydrogenative coupling of alcohols with amines

The Acceptorless Dehydrogenative Coupling (ADC) of alcohols with amines is reported using a heterogeneous Fe-catalyst. The reaction operates under mild conditions with the liberation of dihydrogen and water as the byproducts. The developed ADC strategy is simple, efficient, exhibits wide functional group tolerance and can be scaled up. The present catalytic approach possesses a dual role; acting as a catalyst as well as being magnetically separable. The sustainable reuse of a heterogeneous iron catalyst is also shown.

Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H2: A Catalytic and Mechanistic Study

The catalytic dehydrogenative coupling of alcohols and amines to form aldimines represents an environmentally benign methodology in organic chemistry. This has been accomplished in recent years mainly with precious-metal-based catalysts. We present the dehydrogenative coupling of alcohols and amines to form imines and H2 that is catalyzed, for the first time, by a complex of the earth-abundant Mn. Detailed mechanistic study was carried out with the aid of NMR spectroscopy, intermediate isolation, and X-ray analysis.