37 results about "Hydroboration" patented technology

The present application relates to a kind of catalyst composition and its application in catalytic preparation optically active secondary alcohol, the catalyst composition includes chiral ionic bridged aryloxyalkane rare earth complex and additive, the additive is selected from one or more of pyrimidine, N,N-dicyclohexylmethylamine, 4,4'-dipyridyl.The above-mentioned catalyst composition can be used for synergistically catalyzing asymmetric borohydration of chalcone and its derivatives with pinacol borane, and show high catalytic activity and high enantioselectivity, product yield is as high as 99%, ee value can reach 84%, provide a reliable new way for the efficient, high selective synthesis of optically active secondary alcohol.

The invention discloses p-toluenesulfonic acid 8-tert-butyl diphenyl silyloxy-7-methyl octyl ester as well as a synthesis method and application thereof, and relates to the technical field of biopesticides. The preparation method comprises the following steps: taking 8-bromocaprylic acid as an initial raw material, and firstly reacting with t-BuOK and 18-crown ether-6; then reacting with pivaloyl chloride to generate acid anhydride, and then carrying out acylation reaction with 4-benzyl oxazolidine-2-ketone; then carrying out diastereoselective methylation; then, NaBH4 reduction is carried out; carrying out hydroxyl protection; then carrying out hydroboration oxidation reaction; and then carrying out TsCl sulfonylation, so as to synthesize the p-toluenesulfonic acid-8-tert-butyl diphenyl silyloxy 7-methyl octyl ester. The optical purity of the (S)-p-toluenesulfonic acid 8-tert-butyl diphenyl silyloxy-7-methyl octyl ester synthesized in the invention reaches 98%, and the optical purity of the (R)-p-toluenesulfonic acid 8-tert-butyl diphenyl silyloxy-7-methyl octyl ester synthesized in the invention also reaches 98%.

The invention belongs to the technical field of preparation of catalytic materials, and provides a high-density defective polyacid-based metal organic framework catalyst for hydroboration, a preparation method and application. According to the catalyst, a metal organic framework with defects is constructed by adopting a mixed ligand strategy, a polyacid cluster is introduced in situ on the basis of the metal organic framework, and through weak interaction between a cluster object and a subject framework, regulation and control of an oxidation state of a metal node and regulation and control of a supporting effect of an expanded pore space are realized at the same time; therefore, the problem of unstable structure caused by high defect content is overcome, the polyacid-based metal organic framework catalyst with high-density defects is successfully constructed, the catalyst solves the problems that the existing hydroboration reaction is high in temperature, the catalyst is difficult to recycle and the like, efficient conversion of the alkyne hydroboration reaction can be realized, and the yield of the alkyne hydroboration reaction is increased. Moreover, the structure is still stable after repeated cyclic utilization and use, and can be expanded to various alkyne substrates.

The invention discloses a heat-resistant bio-based degradable polyester material and a preparation method of the heat-resistant bio-based degradable polyester material, and belongs to the field of bio-based high polymer materials. Two brand-new bio-based modified compounds are introduced, wherein one compound is diol with a bicyclic structure prepared by reacting bio-based vanillin with epichlorohydrin and carrying out hydroboration-oxidation, and the other compound is binary acid with an imidazole ring generated by hydrogenating bio-based itaconic acid and condensing the hydrogenated bio-based itaconic acid with ethylenediamine. The preparation method comprises the following steps: melting and mixing 1, 4-butanediol, adipic acid and two modified compounds, adding a catalyst and a nucleating agent, carrying out condensation polymerization under a high-temperature vacuum condition, and drying to obtain the polyester material. According to the material, the heat resistance is synergistically improved through the rigidity of a double-ring structure and the polarity of an imidazole ring, and the material is clear in bio-based source, can be completely biodegraded and is suitable for the fields of high-temperature packaging, degradable meal boxes and the like.

The invention relates to a catalytic system based on at least one neodymocene borohydride, a co-catalyst which is a dialkylmagnesium compound of formula RB-Mg-RL, in which RB is a secondary alkyl of formula R2CH and RL is a primary alkyl of formula RCH2, the Rs, identical or different, being alkyls. The catalytic system addresses the objective of improved macrostructure control in a polymerization process of ethylene or a monomer mixture containing ethylene and a 1,3-diene.

The invention belongs to the technical field of organic synthesis, and particularly discloses a synthesis method of isopinopinone, which comprises the following steps: (1) by taking alpha-pinene as a raw material, hydroborating by using a borane tetrahydrofuran complex, and oxidizing the hydroboration product by using a sodium hydroxide solution and hydrogen peroxide to obtain isopinopinol; (2) performing high-temperature dehydrogenation on the isopinopinol by taking Cu / Ni-Al-SBA-15 as a catalyst to obtain a product, namely isopinopinone; the total loading capacity of Cu and Ni in the Cu / Ni-Al-SBA-15 is 9-12%, the molar ratio of Cu to Ni is (8-10): 1, and the molar ratio of Si to Al in the carrier Al-SBA-15 is (9-11): 1. The conversion rate and the yield of the two-step reaction are relatively high, the dehydrogenation catalyst in the second step can be recycled for more than three times through filtration, and compared with a traditional copper-silicon catalyst, the mesoporous weak-acid molecular sieve serving as a carrier can effectively improve the product selectivity. The purity of the isopinopinone obtained through filtration and rectification can reach 99% or above, the cost can be effectively reduced, and industrial production can be achieved.

The invention belongs to the technical field of organic synthesis, and particularly relates to a branched perfluoropolyether phosphate compound, a composition as well as a preparation method and application of the branched perfluoropolyether phosphate compound. According to the invention, perfluoropolyether alcohol is used as a raw material, and is subjected to substitution, hydroboration and other reactions to prepare the branched perfluoropolyether phosphate compound. The obtained compound has a multi-branched perfluoropolyether chain, after curing, the multi-branched perfluoropolyether group is dissociated on the surface of a metal base material to form a compact perfluoropolyether film layer, excellent hydrophobic and oleophobic properties and smoothness can be provided, in addition, the multi-branched perfluoropolyether is also beneficial to faster energy conversion or release when the compound is stressed, and the performance of the compound is improved. Further, the friction resistance of the coating is favorably improved. Lone pair electrons contained in phosphorus and oxygen heteroatoms in a phosphate group at the tail end of a molecule can be subjected to characteristic adsorption with empty orbits of atoms on the surface of a metal base material, meanwhile, hydroxyl at the tail end of the molecule can also be combined with hydroxyl on the surface of the base material to form hydrogen bonds to be firmly combined with the base material, a compact phosphate protective film is formed, and good protection performance is achieved.

The invention discloses a preparation method of a nucleotide monomer, which comprises the following steps: taking methyl-D-ribofuranoside as an initial raw material, and finally realizing the synthesis of a compound monomer as shown in a formula P through the steps of selective protection, selective deprotection, C-C bond construction, acylating chlorination reaction, basic group introduction through glycosylation, deprotection, hydroboration oxidation and ring closing in sequence. By providing a brand new synthesis method, the reaction yield is improved, the cost of the whole synthesis molecule is reduced, the binding affinity of the prepared target nucleoside monomer serving as a reported drug applied to HCV resistance to RNA can be improved so as to further improve nuclease resistance, and the method has great significance for subsequent nucleic acid drug research.

The invention relates to the field of synthesis of organic compounds, in particular to a hydroboration reaction method for catalyzing ketone by a rare earth metal complex. The method for catalyzing the hydroboration reaction of the ketone by the rare earth metal complex comprises the following steps: mixing the rare earth metal complex, pinacolborane, the ketone and a solvent in an inert atmosphere, and reacting, the general chemical formula of the rare earth metal complex is RE (OTf) 3, and RE is a rare earth element. According to the method for catalyzing the hydroboration reaction of the ketone by using the trifluoromethanesulfonic acid rare earth metal (RE (OTf) 3), the catalyst is a commercial product and is low in price, simple and convenient to operate, high in reaction activity, wide in substrate range and high in yield.

This invention provides a method for the catalytic hydroboration of nitrile compounds, belonging to the field of nitrile reduction technology. The method uses nitrile compounds as substrates, molybdenum hexacarbonyl as a catalyst, and pinacolborane as a hydrogen source, with the hydroboration reaction occurring at 78-82°C for 7.5-8.5 h. The reaction utilizes molybdenum hexacarbonyl as a catalyst, which is simple and readily available, requiring no complex synthesis. Furthermore, the reaction process does not require the participation of ligands. Using pinacolborane as a hydrogen source eliminates the need for strictly nitrogen-protected experimental conditions, enabling the hydroboration of nitriles. The substrate applicability is broad, applicable not only to aromatic nitriles but also to aliphatic nitriles and even some dinitriles. The reaction process does not require solvents, making it environmentally friendly. The corresponding hydroboration product is obtained directly after the reaction without further purification, and the reaction yield is high, ranging from 84-100%.

The invention provides a preparation method of an aminopyrimidine compound, which comprises the following steps: step 1, pretreating a reducing agent by using a protic reagent, the reducing agent being selected from a hydroboration reagent; 2, reacting the pretreated reducing agent with Lewis acid; and step 3, adding a compound 1 into the reaction product in the step 2, and carrying out reduction reaction on the compound 1 to obtain a compound I. The preparation method provided by the invention has the advantages of low cost, short reaction time, high product purity, high yield and the like, and is suitable for industrial production.

The invention discloses an application of a copper-based heterogeneous catalyst in catalysis of alkyne and B2Pin2 hydroboration reaction, and the copper-based heterogeneous catalyst is prepared by the following steps: under stirring, adding a copper salt-containing N, N-dimethylformamide-absolute ethyl alcohol solution into a pyridine-3, 5-dicarboxylic acid-containing N, N-dimethylformamide-absolute ethyl alcohol solution, uniformly mixing, and carrying out vacuum drying, thereby obtaining the copper-based heterogeneous catalyst. Reacting at 100-150 DEG C, cooling to room temperature after the reaction is completed, and carrying out solid-liquid separation, solid washing and drying to obtain the product, the copper-based heterogeneous catalyst disclosed by the invention is simple in preparation process, good in stability and recyclable, the reaction can be completed only in 5 minutes when the copper-based heterogeneous catalyst is used for catalyzing an alkyne hydroboration reaction, the reaction condition is mild, the product selectivity and the yield are relatively high, and the copper-based heterogeneous catalyst has good substrate universality.

The invention discloses a cobalt boron hydrogen complex with a hexahedron structure and a preparation method and application thereof, and belongs to the technical field of cobalt boron cluster complexes. The molecular formula of the cobalt boron hydrogen complex with the hexahedral structure is C30H47Co3B2. The invention further discloses a preparation method of the cobalt boron hydrogen complex with the hexahedral structure. The preparation method of the cobalt boron hydrogen complex comprises the following step: reacting the diaryl bridged double cobalt metal complex with borane-tetrahydrofuran (BH3THF) to prepare the cobalt boron hydrogen complex with a hexahedron structure. The cobalt boron hydrogen complex with the hexahedral structure is applied to a catalyst for catalytic hydrogenation reaction. The cobalt boron hydride complex with the hexahedral structure is prepared by adopting a borane direct coordination mode, so that the use of a reducing agent metal hydroboron is avoided, and the reaction is milder and more controllable. The cobalt boron hydrogen complex with the hexahedron structure has a good application prospect.

The invention discloses a preparation method and application of a foamed phosphorus-doped carbon nitride confinement metal cobalt photo-thermal catalyst, and belongs to the field of photo-thermal catalytic material preparation and hydroboron hydrogen production. According to the preparation method, melamine is treated through a mixed acid solution of hydrochloric acid and phosphoric acid, foamed phosphorus-doped graphite-like phase carbon nitride is obtained in one step by means of self-assembly of a melamine-cyanuric acid supramolecular precursor, then dipping is performed through a cobalt salt solution, Co < 2 + > is subjected to confined adsorption in a foamed carbon nitride structure, and the carbon nitride is prepared. And finally, reducing the foamed phosphorus-doped graphite-like carbon nitride into metal cobalt in situ through NaBH4, so as to prepare the foamed phosphorus-doped graphite-like carbon nitride confinement cobalt photo-thermal catalyst. The foamed structure is beneficial to transmission of reactant molecules, confined cobalt provides more active sites for surface reaction, the forbidden band width of carbon nitride is reduced after phosphorus doping, and the visible light excitation electron transition capability can be enhanced.

The invention provides a method for catalyzing the hydroboration reaction of nitrile compounds, which belongs to the technical field of nitrile reduction, the nitrile compounds are used as a substrate, molybdenum hexacarbonyl is used as a catalyst, pinacolborane is used as a hydrogen source, and the hydroboration reaction is carried out at 78-82 DEG C for 7.5-8.5 hours. Molybdenum hexacarbonyl is used as a catalyst in the reaction and is simple and easy to obtain, complex synthesis is not needed, and in addition, ligand participation is not needed in the reaction process; according to the method, pinacolborane is used as a hydrogen source, the reaction process does not need strict nitrogen protection experiment conditions, the nitrile hydroboration is realized, the substrate application range is wide, and the reaction is not only suitable for aromatic nitrile, but also suitable for fatty nitrile and even some dinitrile; in the reaction process, no solvent is needed, and the method is environment-friendly; after the reaction is finished, a corresponding hydroboration product can be obtained without further purification, and the reaction yield is high and is 84-100%.

This invention discloses a chiral 1,2-diamine-derived N,N,N-tridentate pincer ligand, its synthesis method, and its applications. The structural formula of the ligand is as follows: Ar is a nitrogen donor, which is pyridine, benzimidazole, or quinoline; R is methyl, isopropyl, or tert-butyl. This ligand has a stable structure, is simple to synthesize, and is easy to prepare in large quantities. Under an inert atmosphere, the ligand of this invention coordinates with an iron salt in an organic solvent to obtain a ligand / iron catalyst, which catalyzes the Brown Hydroboration reaction of olefins with high conversion rate, good chemoselectivity, and broad substrate versatility.

The invention relates to silicon-containing three-dimensional center silacyclohexenone skeleton borane as well as a preparation method and application thereof, the silicon-containing three-dimensional center silacyclohexenone skeleton borane has a structural formula as shown in a formula (I), and substituent groups R1 and R2 are respectively aryl or alkyl. According to the synthesis method of the compound, metal copper is used as a catalyst, and under the combined action of a chiral phosphine ligand and alkali, silacyclohexenone and a diborane compound are subjected to a hydroboration reaction to synthesize the compound. The synthesis method provided by the invention is simple to operate, mild in reaction condition, high in substrate universality, high in product yield and high in enantioselectivity. The synthesized compound is an important silicon-containing stereo center heterocyclic compound and can be widely applied to various fields of organic synthesis, medicine, material chemistry and fine chemical engineering.

The present invention relates to a catalytic system based on at least a neodymium borohydride-ferrocene, a dialkyl magnesium compound and a dialkylzinc compound. The catalytic system can be used for homopolymerization of ethylene and copolymerization of ethylene and 1, 3-diene.

The invention relates to the technical field of organic synthesis, and particularly discloses an efficient preparation method of aniline and derivatives thereof. The invention discloses an efficient preparation method of aniline and derivative series products thereof, which comprises the following steps: adding an alkali substance into a mixed solvent system of water and an alcohol substance, and reacting at the temperature of 0-60 DEG C by taking nitrobenzene or a derivative thereof as a reaction substrate, hydroboron as a hydrogen negative reducing agent and protein powder as a cocatalyst, and performing post-treatment to obtain a target product. The dosage of the alkaline substance needs to enable the pH value of the reaction system to be kept above 13; the dosage of the protein powder is 0.5-5% of the weight of the reaction substrate; the dosage of the hydroboron is 1-3 times of the molar dosage of the reaction substrate. The preparation method of aniline and derivatives thereof provided by the invention has the advantages of high safety, low preparation cost, convenience in operation, high reduction efficiency and the like.

This invention discloses a method for synthesizing 2,4,5-trifluorophenylacetic acid, comprising reacting a compound of formula II with a nitro compound in a first reaction, followed by a second reaction with a borohydride to obtain a compound of formula III; the compound of formula III then undergoes a third reaction with a nitrite to synthesize 2,4,5-trifluorophenylacetic acid. This synthetic method uses readily available raw materials, is simple to operate, low in cost, and has a short route. It is also environmentally friendly, safe, and reliable, significantly improving the feasibility of industrial production.

The present invention relates to the field of organic synthesis and, more specifically, it concerns a process for preparing compound of formula (I) by a hydroboration-oxidation reaction of compound of formula (II).

The invention discloses a polynuclear phosphoborane catalyst as well as a preparation method and application thereof, and belongs to the field of chemical synthesis and chemical catalysis. The catalyst is constructed by combining a borane component and an organophosphorus nitrile base ligand, has strong basicity of organophosphorus nitrile base and a multi-center borane Lewis acid site, and can efficiently activate monomers and stabilize active species through acid-base synergism. The preparation method comprises the following steps: taking hexachlorocyclotriphosphazene or octachlorocyclotetraphosphazene as a raw material, carrying out alkylene substitution to obtain a precursor, and reacting the precursor with a hydroboration reagent, so that the synthetic route is simple, and the raw material is easy to obtain. The catalyst can efficiently catalyze epoxide homopolymerization and epoxide and anhydride copolymerization, low-molecular-weight polyether and polyester with controllable structures can be prepared with high selectivity, the molecular weight distribution of the product is narrow, and the application prospect is wide.

This invention discloses a Cu4 cluster catalytic material with synergistic dual catalytic sites and its application in the hydroboration reaction, belonging to the interdisciplinary field of coordination chemistry and nanomaterials. This copper cluster, using N-heterocyclic thiones (methimazole) as protecting ligands, is synthesized in high yield via a simple one-pot method. The chemical formula of the cluster is: C 16 H 20 Cu4N8S4, abbreviated as Cu4NC, belongs to the tetragonal crystal system and has a space group of 1. P 42 / n, a =10.01930(10)Å, b =10.01930(10)Å, c =11.6512(2)Å, α =90°, β =90°, gamma =90°, V =1169.62(3)Å 3 This catalyst utilizes the advantages of its synergistic dual catalytic sites to achieve highly efficient and selective catalytic hydroboration of alkynes. It exhibits excellent chemoselectivity (up to 100%), high efficiency (conversion number (TON) = 77786), high yield (up to 99%), a broad substrate range (28), mild conditions (room temperature and air), and high recovery rate, which are beneficial for the development of functionalized cluster catalysts.

The application belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of 7-ethyl chromanol. The 7-ethyl chromanol is prepared by using 7-ethyl indole-3-methyl aldehyde as a starting material, reacting with methyl triphenyl halogenated phosphorus, and then being subjected to borohydride oxidation. The preparation method can effectively avoid the problems of more impurities, difficult purification and low yield caused by Fischer Indole synthesis method in the prior art, and also effectively avoids the use of toxic KCN, improves the operation safety, and simplifies the production operation without the need of reducing pressure fractionation operation for purifying the target product. The preparation process of the 7-ethyl chromanol is simple in operation, the obtained product has high yield and purity, and is suitable for industrial production.

The application discloses a hyperbranched fluorocarbon surfactant and a preparation method thereof. The fluorocarbon surfactant is prepared by using an iodine-substituted alkane as a substrate and through addition, ring opening, quaternary ammonium, Grignard reaction, borohydride oxidation and other steps. The fluorocarbon surfactant has both hydrophilic groups and hydrophobic groups. The fluorocarbon surfactant with the structure has excellent surface performance. When the fluorocarbon surfactant is compounded with other materials into a foam fire extinguishing agent, the fluorocarbon surfactant can effectively isolate the combustion from air, and plays a role of rapid fire extinguishing.

This invention relates to a method for preparing agomelatine, belonging to the field of pharmaceutical synthesis technology. To address the problems of long, unsafe, and low-yield existing routes, this invention provides a method for preparing agomelatine, comprising: reacting a compound of formula 8 with acetic anhydride to obtain the final product, compound 1 (agomelatine); further comprising reacting a compound of formula 4 with dimethyl sulfate in a mixed solvent of alcohol and water in the presence of an alkali metal hydroxide to obtain compound 5; subjecting compound 5 to hydrogenation reduction under the catalysis of borohydride to obtain compound 6; reacting compound 6 with benzylamine under the action of potassium tert-butoxide to obtain compound 7; and subjecting compound 7 to catalytic hydrogenation reduction under the catalysis of a palladium-containing catalyst to obtain compound 8. This invention features simple post-processing, easier recovery of the palladium catalyst, and high product yield, effectively improving reaction efficiency and safety.

The application discloses a method for synthesizing alkenyl borate ester compounds through a series reaction of palladium-catalyzed cross-coupling and iron-catalyzed borohydration, and belongs to the field of organic synthesis. The method inserts multiple methylene units into the carbon-carbon sigma-bond of the alkenyl borate ester through a series reaction of palladium-catalyzed cross-coupling and iron-catalyzed borohydration, and meanwhile, a valuable C(sp 2 )‑B functional group is reserved. The method utilizes the universality of the alkenyl borate ester in the cross-coupling reaction, provides an efficient approach for modular and iterative synthesis of C(sp3) homologues of bioactive molecules containing olefin structures, and is expected to accelerate the drug discovery process, applied to efficient preparation of drug molecule homologues and complex organic compounds, and provides a powerful tool for realizing rapid structural derivatization of drug lead compounds.

The application discloses a boron-nitrogen doped polycyclic aromatic compound and a synthesis method thereof, and relates to the technical field of organic synthesis. The application takes o-bromonitrobenzene as raw material, and first carries out a Bartoli reaction with vinyl magnesium bromide to synthesize 7-bromoindole; then carries out twice coupling reactions under the action of a metal catalyst to form a dimer of indole; carries out a reaction of the dimer of indole with di-tert-butyl dicarbonate to obtain a single Boc dimer of indole; carries out a borohydration reaction on the single Boc dimer of indole to obtain a boron-containing intermediate; and finally carries out a reaction with a Grignard reagent to obtain the boron-nitrogen doped polycyclic aromatic compound. The synthesis method has the characteristics of a relatively short reaction path, simple operation method and mild reaction conditions. Meanwhile, the compound synthesized by the application is sensitive to fluoride ions and has a high fluorescence quantum yield, and can be applied to the fields of fluoride ion sensors and organic photoelectric materials, and has a wide application prospect.

This invention discloses a method for synthesizing N-amino-3-azabicyclooctane hydrochloride, relating to the field of fine chemical synthesis. The method begins with cyclohexanone to construct 2-formamide-cyclohexanone, followed by chlorination at 0°C to 5°C, and then a ring-condensation rearrangement reaction in methanol at 10°C to 15°C for 10 hours to construct a cyclopentanediimide precursor skeleton. Next, in a zinc chloride and potassium borohydride reduction system, a first reduction salting reaction is performed under reflux with a gradient temperature increase up to 100°C to obtain 3-azabicyclooctane hydrochloride. Finally, a second reduction salting reaction involving nitrosation and zinc powder is carried out sequentially. This invention effectively suppresses side reactions such as ring-opening by precisely controlling the temperature, timing, and feed gradient of the rearrangement and ring-condensation steps, significantly improving the conversion rate of the target skeleton and the purity of the final product.